Sodium Thiosulfate → 2-Acetylamino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906517Notes

Reaction equation

HRID 906517 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH:10]([OH:13])[CH2:11][CH3:12])[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]=1[NH:18][C:19](=[O:21])[CH3:20].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]=1[NH:18][C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 591644582-Acetylamino-5-(1-hydroxy-propyl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 591645072-Acetylamino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-acetylamino-5-(1-hydroxy-propyl)-4-trifluoromethyl-benzoic acid methyl ester (262 mg, 0.82 mmol) in DCM (1.3 mL) was added to a solution of Dess-Martin periodinane (556 mg, 1.31 mmol) in DCM (2.6 mL) and the mixture was stirred for 1 h at r.t. It was then poured into aqueous sodium thiosulfate and this mixture was extracted with EtOAc. The organic phase was then washed twice with aqueous potassium hydrogencarbonate (pH=8), once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give crude 2-acetylamino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester as a white solid which was used without further purification in the next step, ESI-MS: m/z 318 [M+H]+.

Workup

  1. extractionthis mixture was extracted with EtOAc
  2. washThe organic phase was then washed twice with aqueous potassium hydrogencarbonate (pH=8), once with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3528c06ad63482aa793b863a005351c
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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