Ethyl Acetate → {(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester

HRID 20405

Reaction equation

HRID 20405 reaction equation
[I:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14](=[O:28])[NH:15][C@H:16]([CH2:26][OH:27])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:12])([CH3:11])[CH3:10].[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31]OC=C.[C:37]([O:40]CC)(=O)[CH3:38]>C(#N)C>[C:9]([O:13][C:14](=[O:28])[NH:15][C@H:16]([CH:26]([O:40][CH2:37][CH2:38][I:1])[O:27][CH2:36][C:30]([CH3:29])([CH3:31])[CH3:35])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanolHCID 148973511-(Ethenyloxy)-2,2-dimethylpropane

Product 1

HCID 68561131{(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl esterYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Add N-iodosuccinimide (14.19 g, 74.63 mmol) to ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (15.00 g, 53.30 mmol) and 2,2-dimethyl-1-vinyloxypropane (9.13 g, 79.96 mmol) in acetonitrile (267 mL) at room temperature. Heat to 60° C. under nitrogen for 2 hours. Cool to room temperature and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as an oil (23.4 g 84.2%).

Workup

  1. temperatureCool to room temperature
  2. washWash with water and saturated aqueous sodium chloride
  3. dry with materialDry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-bffe4dffcbdc41dca34b21a93476b393
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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