N-(Benzyloxycarbonyl)-D-proline
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N-(Benzyloxycarbonyl)-D-proline
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CAS No:
6404-31-5
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Formula:
C13H15NO4
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Chemical Name:
N-(Benzyloxycarbonyl)-D-proline
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Synonyms:
1,2-Pyrrolidinedicarboxylic acid,1-(phenylmethyl) ester,(2R)-;1,2-Pyrrolidinedicarboxylic acid,1-benzyl ester,D-;1,2-Pyrrolidinedicarboxylic acid,1-(phenylmethyl) ester,(R)-;(Benzyloxycarbonyl)-D-proline;N-(Benzyloxycarbonyl)-D-proline;1-(Benzyloxycarbonyl)-D-proline;N-(Benzyloxycarbonyl)-(R)-proline;N-Carbobenzyloxy-D-proline;(2R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid;(R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid;(R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid;D-Cbz-Proline;(2R)-1-Phenylmethoxycarbonylpyrrolidine-2-carboxylic acid;(2R)-1-[(Benzyloxy)carbonyl]pyrrolidine-2-carboxylic acid;(R)-N-BenzyloxycarbonyLproline;196810-31-8
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CAS No:
N-(Benzyloxycarbonyl)-D-proline Basic Attributes
249.26
249.26
485188
229-021-5
DTXSID60214085
29339900
Characteristics
66.8
1.7
White Crystalline Powder or Powder
1.3±0.1 g/cm3
76.5-77.5 °C
432.3°C at 760 mmHg
215.3±28.7 °C
1.582
Store at RT.
40 º (c=2, EtOH)
Safety Information
NONH for all modes of transport
3
24/25
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H302 (14.29%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 8 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
N-(Benzyloxycarbonyl)-D-proline Use and Manufacturing
Step-1 : Preparation of (R)-l-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a) To a stirred solution of D-Proline (1.2 g, 10.42 mmol) in 2 N aqueous NaOH solution (20.85 mL, 41.7 mmol) at 0 °C was added benzyl chloroformate (1.488 mL, 10.42 mmol) and allowed to warm to room temperature overnight. The reaction was washed with MTBE (2 x 25 mL), acidified with cone HCl and extracted with ethyl acetate (2 x 200 mL). The ethyl acetate layers were combined washed with water (50 mL), brine (25 mL) dried and concentrated in vacuum to afford (R)-l-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a) (2.41 g, 9.67 mmol, 93 percent yield) which was used as such in next step; Η NMR (300 MHz, DMSO-i) δ 12.66 (s, 1H), 7.42 - 7.25 (m, 5H), 5.14 - 4.97 (m, 2H), 4.20 (ddd, J = 22.7, 8.8, 3.5 Hz, 1H), 3.50 - 3.25 (m, 2H), 2.32 - 2.08 (m, 1H), 1.97 - 1.75 (m, 3H); MS (ES+) 250.2 (M+l), 272.2 (M+Na), (ES-) 248.2 (M-l), 284.2 (M+Cl), 497.4 (2M-1).20.0mmol D-valine was dissolved in 12.0mL, 2mol/L NaOH solution, 22mmol benzyl chloroformate was added dropwise at 0 °C, then added with NaOH solution, extracted, washed, dried, concentrated, separated by silica gel column. Got(R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid in a yield of 95percent.
Computed Properties
Molecular Weight:249.26
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:249.10010796
Monoisotopic Mass:249.10010796
Topological Polar Surface Area:66.8
Heavy Atom Count:18
Complexity:312
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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