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

HRID 1664715Notes

Reaction equation

HRID 1664715 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-a20cf45da65641ecad90c69115b7f38e
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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