Trifluoroacetic acid → 3,N-Dihydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionamide

HRID 2212562Notes

Reaction equation

HRID 2212562 reaction equation
C(O[C:4](=[O:29])[C:5]([CH3:28])([CH3:27])[CH:6]([OH:26])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([CH3:25])[CH:16]=2)=[CH:9][CH:8]=1)C.[OH-:30].[K+].[NH2:32]O.CO.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C1COCC1>[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37].[OH:26][CH:6]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([CH3:25])[CH:16]=2)=[CH:9][CH:8]=1)[C:5]([CH3:27])([CH3:28])[C:4]([NH:32][OH:30])=[O:29]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 695964293-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl esterHCID 86760235KOH NH2OH MeOH

Product 2

HCID 6422Trifluoroacetic acidHCID 98428493,N-Dihydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionamideYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester (0.10 g, 0.25 mmol) in THF (1 mL) was treated with a solution of KOH/NH2OH/MeOH (3 mL) under nitrogen at room temperature. The reaction was stirred for 1.5 h, acidified with TFA and concentrated. The product was purified by HPLC on a C-18 column eluting with an acetonitrile:water:TFA gradient to give the title compound (0.51 g, 54%) as a white solid. MS found: (M+H)+=381.

Workup

  1. concentrationconcentrated
  2. customThe product was purified by HPLC on a C-18 column
  3. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-c9ab0df4dbac4204a9add2545032820c
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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