N-Acetyl-L-proline
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N-Acetyl-L-proline
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CAS No:
68-95-1
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Formula:
C7H11NO3
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Chemical Name:
N-Acetyl-L-proline
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Synonyms:
L-Proline,1-acetyl-;Proline,1-acetyl-,L-;1-Acetyl-L-proline;1-Acetylproline;N-Acetylproline;N-Acetyl-L-proline;L-N-Acetylproline;(S)-N-Acetylproline;(S)-(-)-N-Acetylproline;NSC 280718;(S)-1-Acetylpyrrolidine-2-carboxylic acid;(2S)-1-Acetylpyrrolidine-2-carboxylic acid;(S)-AcetyLproline
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CAS No:
Description
white to off-white powder
N-acetyl-L-proline is a N-acetyl-L-amino acid, a N-acylpyrrolidine, a pyrrolidinemonocarboxylic acid and a L-proline derivative.
Characteristics
57.6
-0.7
White to off-white Powder
1.3±0.1 g/cm3
106 °C
366.2°C at 760 mmHg
175.3±25.9 °C
1.517
>23.6 [ug/mL]
2-8°C
-86 º (c=1 EtOH)
140.3 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|133.7 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|136.9 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
N-Acetyl-L-proline Use and Manufacturing
115.1 mg (1 mmol) of L-proline, Add the right amount of solvent methanol dissolved, The amount of acetic anhydride syringe 0.3mL (about 3mmol)DIEA0.5mL (about 3mmol) was added to the reaction system, 70 reflux reaction 7h. Completed the reaction, The methanol in the reaction solution was removed under reduced pressure and the unreacted acetic anhydride was removed by freeze-drying.Prepared by HPLC (mobile phase methanol: water = 45: 65 with 0.05percent formic acid, UV wavelength 214 nm)Obtained as a white solid in 84.2percent yield.To a solution of (S)-pyrrolidine-2-carboxylic acid (1.0 g) in DCM (20 mL) was added acetic anhydride (2.7 g). The resulting mixture was stirred at 30°C overnight and concentrated in vacuo. Cold water (30 mL) was added, and the aqueous layer was extracted with DCM(2x100 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give (S)-1-acetylpyrrolidine-2- carboxylic acid (500 mg) as a white solid. MS(ES) mlz 158 (MH).To a suspension of l-proline (4.34 mmol, 500 mg) in tetrahydrofuran was added acetyl chloride (20 mL) at room temperature and the reaction mixture was refluxed for 2 h.
N-Acetyl-L-proline is an aminoacid used in the synthesis of pharmaceutical compounds useful in preventing and treating disorders and syndromes associated with the nervous, vascular, musculoskeletal, or cutaneous systems.
Computed Properties
Molecular Weight:157.17
XLogP3:-0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:157.07389321
Monoisotopic Mass:157.07389321
Topological Polar Surface Area:57.6
Heavy Atom Count:11
Complexity:190
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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