Imidazole → 2-[(tert-butoxy)carbonylamino]-3-hydroxy-N-(phenylmethoxy)-4-(1,1,2,2-tetramethyl-1-silapropoxy)butanamide

HRID 1397815Notes

Reaction equation

HRID 1397815 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:21]([OH:24])[CH2:22][OH:23])[C:10]([NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].O>ClCCl.CN(C)C=O.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH:21]([OH:24])[CH2:22][O:23][Si:30]([CH3:32])([CH3:31])[C:33]([CH3:36])([CH3:35])[CH3:34])[C:10]([NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962Water2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 86639529[(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy)butanamide

Product 1

HCID 866395312-[(tert-butoxy)carbonylamino]-3-hydroxy-N-(phenylmethoxy)-4-(1,1,2,2-tetramethyl-1-silapropoxy)butanamideYield 44.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

[(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy) butanamide (47 g, 138 mmol), imidazole (37.5 g, 552 mmol) and tert-butyldimethylsilyl chloride (57.7 g, 386.4 mmol) were stirred at 0° C. for 1 h and the room temperature for an additional 1 h in a mixture of dichloromethane (1.7 L) and dimethylformamide (17 mL). Water (250 mL) was added and after decantation, water (2×250 mL) and brine (250 mL) was used for washing the organic phases, which was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography using a mixture of ethyl acetate/hexane (1/4) as eluent to get 28 g of the desired product.

Workup

  1. washfor washing the organic phases, which
  2. dry with materialwas dried over Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by column chromatography
  5. additiona mixture of ethyl acetate/hexane (1/4) as eluent

Sources & evidence

ORD record
ord-87a1cf2826b5400d9af66ebbcef05337
Source dataset
uspto-grants-2014_12
Patent number
US08901293B2

Reaction notes

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