Chlorotrimethylsilane → Methyl (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoate

HRID 1913325Notes

Reaction equation

HRID 1913325 reaction equation
[CH3:1][Si](Cl)(C)C.[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:21][C:22]([F:31])([F:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([OH:20])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH2:21][C:22]([F:30])([F:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([O:20][CH3:1])=[O:19])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 66661204(S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoic acid

Product 1

HCID 57535357Methyl (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl chloride (0.61 g, 5.61 mmol, 2 eq) was added dropwise to a solution of (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoic acid (1.02 g, 2.81 mmol) in 40 ml of methanol. After the addition had ended, the mixture was stirred at RT for 3 h. The solvent was removed under reduced pressure and the residue was used crude in the reaction which followed.

Workup

  1. additionAfter the addition
  2. customThe solvent was removed under reduced pressure
  3. customin the reaction which

Sources & evidence

ORD record
ord-0d2646dd8ed1481381900b34b18cb8a1
Source dataset
uspto-grants-2013_12
Patent number
US08609681B2

Reaction notes

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