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Sodium Chloride → [(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

HRID 20339
Notes
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Reaction equation

HRID 20339 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([O:23][CH2:24][CH3:25])=C.[I:26]N1C(=O)CCC1=O.[Cl-].[Na+].[C:36](#N)[CH3:37]>>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH:9]([O:23][CH2:24][CH2:25][I:26])[O:10][CH2:36][CH3:37])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 6342AcetonitrileHCID 8023Ethyl vinyl etherHCID 120273N-IodosuccinimideHCID 10913779(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol

Product 1

HCID 86615364
[(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester
Yield 34%

Procedure

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

Workup

  1. extractionExtract with ethyl acetate
  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 100:0 to 10:90 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-86666333ce9343dcba6d302be914e1c2
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes