Trifluoroacetic acid → (2R, 4R)-4-Methoxy-pyrrolidine-2-carboxylic acid [2-fluoro-4-(2-oxo-piperidin-1-yl)-phenyl]-amide

HRID 2217462Notes

Reaction equation

HRID 2217462 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:31])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]2=[O:29])=[CH:19][C:18]=1[F:30])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:30][C:18]1[CH:19]=[C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]2=[O:29])[CH:21]=[CH:22][C:17]=1[NH:16][C:15]([C@H:9]1[CH2:10][C@@H:11]([O:13][CH3:14])[CH2:12][NH:8]1)=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11154790(2R,4R)-2-[2-Fluoro-4-(2-oxo-piperidin-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11416392(2R, 4R)-4-Methoxy-pyrrolidine-2-carboxylic acid [2-fluoro-4-(2-oxo-piperidin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 8 (0.329 g, 0.761 mmol) in anhydrous CH2Cl2 (5 mL) was added TFA (5 mL). The solution was stirred at RT for 0.5 h before concentrating under reduced pressure to reveal 9 (0.255 g, 100%) as a tan oil.

Workup

  1. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-0f7bd9a2ae9049aba23ddafd5860c802
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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