Trimethylsilyl iodide → HCID 54075624, compound

HRID 1061651Notes

Reaction equation

HRID 1061651 reaction equation
I[Si](C)(C)C.C(OC([NH:16][C@@H:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:18]([C:20]1[S:21][CH2:22][CH2:23][N:24]=1)[OH:19])=O)C1C=CC=CC=1>C(#N)C>[NH2:16][C@@H:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:18]([C:20]1[S:21][CH2:22][CH2:23][N:24]=1)[OH:19]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 60073854HCID 60073854, compound

Product 1

HCID 54075624HCID 54075624, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (10 ml) is added to a solution of (1RS,2S)-2(benzyloxycarbonyl)amino-1-(4,5-dihydro-1,3-thiazol-2-yl)-3-phenyl-1-propanol (650 mg, Reference compound No. 11-1) in acetonitrile (10 ml), and the mixture is stirred for 30 minutes. The reaction mixture is concentrated under reduced pressure, ethyl acetate is added to the resulting residue, and the whole is extracted with 1 N hydrochloric acid. Sodium hydrogencarbonate is added to the extract to basify the system, and the whole is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (323 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, ethyl acetate
  2. additionis added to the resulting residue
  3. extractionthe whole is extracted with 1 N hydrochloric acid
  4. additionSodium hydrogencarbonate is added to the
  5. extractionextract
  6. extractionthe whole is extracted with ethyl acetate
  7. washThe extract is washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-39b3ab74aa694376baef01076222eb8e
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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