Trifluoroacetic acid → (R)-1-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-pyrrolidine-2-carboxylic acid

HRID 1691925Notes

Reaction equation

C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:44])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]3[N:30]=[C:31]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:32][C:33]=3[C:34]([F:37])([F:36])[F:35])=[O:28])=[CH:22][N:21]=2)=[CH:16][CH:15]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[C:38]1([C:31]2[O:32][C:33]([C:34]([F:35])([F:36])[F:37])=[C:29]([C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([C:17]4[CH:18]=[CH:19][C:14]([C:13]([N:9]5[CH2:10][CH2:11][CH2:12][C@@H:8]5[C:6]([OH:7])=[O:5])=[O:44])=[CH:15][CH:16]=4)=[N:21][CH:22]=3)=[O:28])[N:30]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66738324(R)-1-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 57651999(R)-1-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-pyrrolidine-2-carboxylic acidYield 80.4%

Procedure

(R)-1-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (37 mg) from above was treated with 2 mL of trifluoroacetic acid and stirred at room temperature for one hour. The reaction was concentrated and the product was lyophilized to give 27 mg of (R)-1-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-pyrrolidine-2-carboxylic acid as a white powder. LCMS calcd for C28H21F3N4O5 (m/e) 550, obsd 551 (M+H).

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-d25127ed7772474694c22cbd32c970aa
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153644B2

Reaction notes

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