Chloroacetyl chloride → 2-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutyl]acetamide

HRID 1022580Notes

Reaction equation

HRID 1022580 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)([OH:8])[CH2:5][O:6][CH3:7].C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1>[Cl:24][CH2:25][C:26]([NH:1][CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)([OH:8])[CH2:5][O:6][CH3:7])=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66975521(2RS)-4-amino-2-(3,4-dichlorophenyl)-1-methoxybutan-2-ol

Product 1

HCID 669764072-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS)-4-amino-2-(3,4-dichlorophenyl)-1-methoxybutan-2-ol (3.00 g) and triethylamine (1.60 mL) in THF (50 mL) was added dropwise chloroacetyl chloride (0.91 ml) under ice-cooling, and the mixture was stirred for 20 min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium 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 (2.13 g).

Workup

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

Sources & evidence

ORD record
ord-b988b9963ff24bce8e868bd3f8d721c3
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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