Trifluoroacetic acid → Repaglinide

HRID 1034032Notes

Reaction equation

HRID 1034032 reaction equation
[CH2:1]([O:3][C:4]1[CH:16]=[C:15]([CH2:17][C:18]([NH:20][C@H:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH:14]=[CH:13][C:5]=1[C:6]([O:8]C(C)(C)C)=[O:7])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:16]=[C:15]([CH2:17][C:18]([NH:20][C@H:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH:14]=[CH:13][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53472587tert.butyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoate

Product 1

HCID 65981Repaglinide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.395 mMol) of tert.butyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoate (melting point: 122°-123° C.; [α]D20 =+8.7°; c=1 in methanol) are stirred into 2 ml of methylene chloride together with 0.45 g (3.95 mMol) of trifluoroacetic acid overnight at ambient temperature. The mixture is evaporated down in vacuo and the evaporation residue is distributed between aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic extract is dried, filtered and evaporated down in vacuo. The evaporation residue is crystallised from ethanol/water (2/1).

Workup

  1. customThe mixture is evaporated down in vacuo
  2. extractionThe organic extract
  3. customis dried
  4. filtrationfiltered
  5. customevaporated down in vacuo
  6. customThe evaporation residue is crystallised from ethanol/water (2/1)

Sources & evidence

ORD record
ord-05167a79f4884869851d9e4d0d8285a0
Source dataset
uspto-grants-1994_05
Patent number
US05312924

Reaction notes

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