Water → HCID 66975923, compound

HRID 1022644Notes

Reaction equation

HRID 1022644 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)[CH:11]([OH:21])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:37][CH2:38][C:39](Cl)=[O:40].O>C1COCC1>[CH2:1]([N:8]([CH2:9][CH:10]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)[CH:11]([OH:21])[CH2:12][O:13][Si:14]([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:16])[CH3:15])[C:39](=[O:40])[CH2:38][Cl:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66976278HCID 66976278, compound

Product 1

HCID 66975923HCID 66975923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2RS,3RS)-4-(benzylamino)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-(3,4-dichlorophenyl)butan-2-ol (6.40 g) and triethylamine (2.16 mL) in THF (50 mL) was added dropwise chloroacetyl chloride (1.23 mL) at 0° C. The mixture was stirred at 0° C. for 20 min, water was added, 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%-30%)) to give the title compound (6.83 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%-30%))

Sources & evidence

ORD record
ord-1741714fce7d4445a5fc96cb8f26f445
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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