Trifluoroacetic acid → {3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydrobenzooxazol-5-yl)-propyl]-benzoylamino}-acetic acid

HRID 2386897Notes

Reaction equation

HRID 2386897 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][NH:8][C:9](=[O:36])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:34])[C:17]([OH:33])([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28](=[O:30])[N:27]([CH3:31])[C:26]=3[CH:32]=2)[C:18]([F:21])([F:20])[F:19])=[C:12]([Cl:35])[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:35][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[CH:16]([CH3:34])[C:17]([OH:33])([C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28](=[O:30])[N:27]([CH3:31])[C:26]=2[CH:32]=1)[C:18]([F:20])([F:21])[F:19])[C:9]([NH:8][CH2:7][C:6]([OH:37])=[O:5])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66697004{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydrobenzooxazol-5-yl)-propyl]-benzoylamino}-acetic acid tert-butyl ester

Product 1

HCID 66697055{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydrobenzooxazol-5-yl)-propyl]-benzoylamino}-acetic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydrobenzooxazol-5-yl)-propyl]-benzoylamino}-acetic acid tert-butyl ester (20 mg, obtained in Example 231) was dissolved in dry dichloromethane (1.0 mL) and trifluoroacetic acid (0.41 mL) was added. The mixture was then allowed to stir at r.t. for 12 hours. The reaction mixture was concentrated in vacuo and the residue was further purified by repeated evaporation from ether (2 times), methanol (2 times) and again dichloromethane (2 times) to give the title compound {3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydrobenzooxazol-5-yl)-propyl]-benzoylamino}-acetic acid as a colorless solid (18 mg). MS (m/e, ISP neg. ion)=485.1 [M−H+].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was further purified
  3. customevaporation from ether (2 times), methanol (2 times) and again dichloromethane (2 times)

Sources & evidence

ORD record
ord-5ee3356727a148dea2b466a9f9207233
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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