Trifluoroacetic acid → Trifluoroacetic acid

HRID 2212567Notes

Reaction equation

HRID 2212567 reaction equation
C[O:2][C:3](=O)[CH:4]([CH3:26])[CH:5]([OH:25])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:24])[CH:15]=2)=[CH:8][CH:7]=1.[OH-:28].[K+].[NH2:30]O.CO.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>>[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35].[OH:25][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:24])[CH:15]=2)=[CH:8][CH:7]=1)[CH:4]([CH3:26])[C:3]([NH:30][OH:28])=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 695964113-Hydroxy-2-methyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid methyl esterHCID 86760235KOH NH2OH MeOH

Product 2

HCID 6422Trifluoroacetic acidHCID 103615373,N-Dihydroxy-2-methyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionamide

Procedure

3-Hydroxy-2-methyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid methyl ester (0.10 g, 0.27 mmol) was added to a solution of KOH/NH2OH/MeOH (2 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred for 1 h and was acidified with TFA. The solution was concentrated and the product was purified by HPLC on a C-18 column eluting with an acetonitrile:water:TFA gradient to give the title compound as two separated diasteromers (0.063 g, 48%) and (0.035 g, 27%) as a white solid. MS found: (M+H)+=367.

Workup

  1. concentrationThe solution was concentrated
  2. customthe product was purified by HPLC on a C-18 column
  3. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-0c6c76c2564b476698a4eb9384973d53
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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