Trifluoroacetic acid → HCID 66881221, compound

HRID 1784054Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:18])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:7]1[C:19](=[O:44])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])=[CH:29][C:28]2=[O:42])=[CH:23][C:22]=1[F:43])=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:18])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:7]1[C:19](=[O:44])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:29][C:28]2=[O:42])=[CH:23][C:22]=1[F:43])=[O:5])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66881971HCID 66881971, compound

Product 1

HCID 66881221HCID 66881221, compoundYield 69%

Conditions

Temperature: 75 °C

Procedure

A solution of 49 mg (0.08 mmol) of (1SR,2SR,3RS)-2-[4-(4-tert-butoxycarbonylmethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-3-(4-chloro-phenylcarbamoyl)-cyclopropanecarboxylic acid ethyl ester in 3 ml of 1,2-dichloromethane was treated with 28 ul of trifluoroacetic acid and stirred at 75° C. during 40 min. Evaporation of the solvents gave 31 mg (69%) (1SR,2SR,3RS) 2-[4-(4-carboxymethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-3-(4-chloro-phenylcarbamoyl)-cyclopropanecarboxylic acid ethyl ester. Off-white solid. MS: 571 (M−H)−.

Workup

customEvaporation of the solvents

Sources & evidence

ORD record: ord-f88b300ee6cc4b8eab49e12e227ee7d7
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501413B2

Reaction notes

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