Water → 2-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906523Notes

Reaction equation

HRID 906523 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25](=[O:45])[C:26]1[CH:31]=[C:30]([CH:32]([OH:36])[CH2:33][CH2:34][CH3:35])[C:29]([C:37]([F:40])([F:39])[F:38])=[CH:28][C:27]=1[NH:41][C:42](=[O:44])[CH3:43].O.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:23][O:24][C:25](=[O:45])[C:26]1[CH:31]=[C:30]([C:32](=[O:36])[CH2:33][CH2:34][CH3:35])[C:29]([C:37]([F:38])([F:40])[F:39])=[CH:28][C:27]=1[NH:41][C:42](=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 585329282-Acetylamino-5-(1-hydroxy-butyl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 585329572-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Dess-Martin periodinane (514 mg, 1.18 mmol) in DCM (2.5 mL) at r.t. was added 2-acetylamino-5-(1-hydroxy-butyl)-4-trifluoromethyl-benzoic acid methyl ester (245 mg, 0.735 mmol). The reaction was stirred at r.t. for 1 h then diluted with EtOAc and poured onto 1:1 mixture water/sat. aq Na2SO3. The organic phase was washed twice with aq KHCO3, brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give the title compound (237 mg, 97% yield) as a beige product. ESI-MS: m/z 332 [M+H]+, m/z 330 [M−H]−.

Workup

  1. washThe organic phase was washed twice with aq KHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e1f4000298ba4e09b5920613cf8e4d02
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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