Trifluoroacetic acid → Pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 1861312Notes

Reaction equation

HRID 1861312 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:29])[NH:14][CH:15]1[CH2:19][C:18](=[O:20])[O:17][CH:16]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:22]([O:21][CH:16]1[CH:15]([NH:14][C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:29])[CH2:19][C:18](=[O:20])[O:17]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 184690272-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 54539738Pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 118 (405 mg, 1.0 mmol) was treated with TFA (2 mL) in CH2Cl2 (2 mL) for one hour. The reaction solution was evaporated in vacuo and azeotrapped with CH2Cl2 four times to give pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide as a pale yellow solid. 1H-NMR (500 MHz, CDCl3): δ 1.87-2.15 (m, 4H), 2.30-2.70 (m, 2H), 2.80-3.08 (m, H), 3.45 (br, 2H), 4.35-4.98 (m, 3H), 5.30-5.56 (m, H), 7.10-7.60 (m, 5H); Analytical HPLC: 7.78/8.20 min.; LC-MS: m/e=305 (M+H+).

Workup

  1. customThe reaction solution was evaporated in vacuo

Sources & evidence

ORD record
ord-1074ba5cd0874442b5c1c9af7b3e39c3
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

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