Water → HCID 66976278, compound

HRID 1022643Notes

Reaction equation

HRID 1022643 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:9]([NH:16][CH2:17][CH:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[CH:19]([OH:22])[CH2:20][OH:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>C1COCC1>[CH2:9]([NH:16][CH2:17][CH:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[CH:19]([OH:22])[CH2:20][O:21][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 66975619HCID 66975619, compound

Product 1

HCID 66976278HCID 66976278, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyldimethylchlorosilane (3.65 g) in THF (10 mL) was added dropwise to a solution of (2RS,3RS)-4-(benzylamino)-3-(3,4-dichlorophenyl)butane-1,2-diol (7.50 g) and triethylamine (9.22 mL) in THF (35 ml) at 0° C. Under nitrogen purging, the mixture was stirred at room temperature for 3 hr, water was added at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-100%)) to give the title compound (6.42 g) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-100%))

Sources & evidence

ORD record
ord-caf0c43aa09d427dad15ba85ab6b6e93
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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