Ethyl Acetate → [(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

HRID 20394

Reaction equation

HRID 20394 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I:35]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][O:19][C:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:28][I:35])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 107401,1-DiphenylethyleneHCID 120273N-IodosuccinimideHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

Product 1

HCID 68558007[(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.

Workup

  1. washwash with saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify on silica gel
  6. washeluting with 0:100 to 30:70 ethyl acetate

Sources & evidence

ORD record
ord-d84c6867d5d949f78021d1ce8021af7c
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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