HCID 86646668, compound → HCID 66725145, compound

HRID 1799214Notes

Reaction equation

HRID 1799214 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:15][NH:16]C(=O)C(F)(F)F)[CH2:10][C:11]([O:13]C)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]>CO.[OH-].[Na+]>[NH2:16][CH2:15][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([NH2:1])[CH:3]=1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 86646668HCID 86646668, compound

Product 1

HCID 66725145HCID 66725145, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Two-hundred (200) mg of methyl (3R)-3-(3-amino-4-chlorophenyl)-4-(2,2,2-trifluoroacetylamino)butanoate (65b) was dissolved in 2.5 mL of methanol and 0.2 mL of 2N sodium hydroxide, the reaction mixture was stirred at room temperature for 16 hours, the solvent was removed under reduced pressure, and the residue purified by preparative HPLC to provide 90 mg of the title compound (65c). 1H NMR (400 MHz, CD3OD): δ 7.21 (d, J=8.0 Hz, 1H), 6.83 (s, 1H), 6.65 (d, J=8.0 Hz, 1H), 3.30-3.26 (m, 2H), 3.15-3.11 (m, 1H), 2.74 (dd, J=16.4, 6.4 Hz, 1H), 2.62 (dd, J=16.4, 6.4 Hz, 1H); MS (ESI) m/z 229.0 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-d5d916f8260144b38fa489511b7aa312
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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