(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate
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![(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/2cdf6ff22d064aea851737bc446bea9d.png "(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate")
(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate
structure -
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CAS No:
96034-64-9
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Formula:
C15H19N3O5S
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Chemical Name:
(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate
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Synonyms:
1-Pyrrolidinecarboxylic acid,2-[(dimethylamino)carbonyl]-4-mercapto-,(4-nitrophenyl)methyl ester,(2S,4S)-;1-Pyrrolidinecarboxylic acid,2-[(dimethylamino)carbonyl]-4-mercapto-,(4-nitrophenyl)methyl ester,(2S-cis)-;(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate;(2S,4S)-2-Dimethylaminocarbonyl-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine;(2S,4S)-N,N-Dimethyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine-2-carboxamide;158168-79-7
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CAS No:
(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate Basic Attributes
353.39
353.39
1806241-263-5
DTXSID20446628
2933990090
Characteristics
96.7
1.5
White Crystalline Solid
1.4±0.1 g/cm3
118-119 °C
555.8°C at 760 mmHg
289.9±30.1 °C
1.612
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(4-Nitrophenyl)methyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylate Use and Manufacturing
The reaction flask was charged with 600 mL of DMF, and 179.5 g (0.55 mol) of (2S, 4S) -1- Carboxy-4-mercaptopyrrolidine (Formula VI) was prepared by reducing the temperature to 0 ° C to 5 ° C, adding 66.8 g (0.66 mol) Diisopropylethylamine, After stirring for 10 minutes, 89.7 g (1.10 mol) of dimethylamine hydrochloride was added and the mixture was stirred at 0 ° C to 5 ° C After 3 hours of reaction, 500 mL of purified ice water was quickly added, and a large amount of solid was precipitated under stirring. After filtration, the cake was washed with 200 mL of water , And dried under reduced pressure at 65 ° C for 15 hours to obtain 179.4 g of (2S, 4S) -1-p-nitrobenzyloxycarbonyl-2- (N, N-dimethylcarbamoyl Yl) -4-mercaptopyrrolidine (Formula VII), 92.3percent molar yield, HPLC purity 99.3percent. Compound VII mass spectrometry data are as follows: C15H19N3O5S, molecular weight: 353.4, [M + H] & lt; + & gt ;: 354.6.Reaction bottle by adding 600 ml of DMF, added under stirring embodiment 6 of preparing 179.5g (0.55mol) (2S, 4S) 1-P-nitro-benzyloxy-carbonyl-2-carboxy-4-mercapto-pyrrolidine (formula VI), cooling to 0 °C to the 5 °C, adding 66.8g (0.66mol) diisopropyl ethylamine, stirring 10 minutes after adding 89.7g (1.10mol) dimethylamine hydrochloride, thermal insulation in the 0 °C to the 5 °C stirring reaction under 3 hours to fast after 500 ml purified ice water, solid precipitating a large amount under stirring, filtering, with 200 ml is currently alkane wash, 65 °C reduced pressure drying under 15 hours, to obtain 179.4g (2S, 4S) 1-P-nitro-benzyloxy-carbonyl-2 - (N, N-di-carbamoyl) - 4-mercapto-pyrrolidine (formula VII), molar yield 92.3percent, HPLC purity 99.3percent.Bi[(2S, 4S)-2-dimethylaminocarbonyl-l-PNZ-pyrrolindin-4-yl]disulfide (XXIII) (15 g, 21 mmol) was suspended in the mixed solvent of tetrahydrofunan (80 ml) and water (80 ml). Under the nitrogen atmosphere, n-tributylphosphine (6g, 60mmol) was added dropwise with stirring. After stirring for 30 min, ethyl acetate (200 ml) and water (200 ml) was added and stirred. The organic phase was dried with anhydrous magnesium sulfate, and evaporated under vacuum to remove solvent. To the residue was added ethyl acetate (100 ml), and the mixture was stirred to crystallize. After substantive crystals were precipitated, petroleum ether (50 ml) was added, and the mixture was filtered to collect crystals. The crystals were dried to give (2S, 4S)-2-dimethylaminocarbonyl-4-thio-l-PNZ-pyrrolindine (XX) (13.5g, yield 90percent) as pale yellow crystal. Mp: 118.5- 119.5Bi[(2S, 4S)-2-dimethylaminocarbonyl-l-PNZ-pyrrolindin-4-yl]disulfide (XXIII) (15 g, 21 mmol) was suspended in the mixed solvent of tetrahydrofunan (80 ml) and water (80 ml). Under 4-Nitrobenzyl (25', 45)-4-(acetylthio)-2-[(dimethylammo)carbonyl]pyrrolidine- 1 - carboxylate (50 g) was suspended in methanol (250 mL), followed by the addition of acetyl chloride (10 g). The reaction mixture was stirred for 5 hours at about 25
Side chain for meropenem Meropenem Intermediate
Computed Properties
Molecular Weight:353.4
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:353.10454189
Monoisotopic Mass:353.10454189
Topological Polar Surface Area:96.7
Heavy Atom Count:24
Complexity:488
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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