Trifluoroacetic acid → (2R,4R)-4-[(4-Methoxy-pyrrolidine-2-carbonyl)-amino]-benzoic acid methyl ester

HRID 2217587Notes

Reaction equation

HRID 2217587 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:27])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][O:25][C:23](=[O:24])[C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]([C@H:9]2[CH2:10][C@@H:11]([O:13][CH3:14])[CH2:12][NH:8]2)=[O:27])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68808041(2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68815558(2R,4R)-4-[(4-Methoxy-pyrrolidine-2-carbonyl)-amino]-benzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 7 (12.5 g, 33.0 mmol) in anhydrous CH2Cl2 (70 mL) was added TFA (20 mL). The solution was stirred at RT overnight before concentrating under reduced pressure to give 8 (9.19 g, 100%).

Workup

  1. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-9432a9e6745845d9a3147a3ecbe6fb60
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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