Dichloromethane → HCID 76831232, compound

HRID 1186168Notes

Reaction equation

HRID 1186168 reaction equation
[NH2:1][C:2]1([C:7]2[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:8]=2[F:14])[CH2:4][CH:3]1[CH2:5][OH:6].ClCCl.[Cl:18][CH2:19][C:20](Cl)=[O:21]>C([O-])(O)=O.[Na+].O.[Cl-].[Na+].O.C(OCC)(=O)C>[Br:13][C:11]1[CH:10]=[CH:9][C:8]([F:14])=[C:7]([C:2]2([NH:1][C:20](=[O:21])[CH2:19][Cl:18])[CH2:4][CH:3]2[CH2:5][OH:6])[CH:12]=1

Participants

8

Reactant 3

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 76831113HCID 76831113, compound

Product 1

HCID 76831232HCID 76831232, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a vigorously stirred mixture of [(1RS,2SR)-2-amino-2-(5-bromo-2-fluoro-phenyl)-cyclopropyl]-methanol (intermediate B8A) (387 mg, 1.49 mmol) in sat. aqueous NaHCO3-sol. (5 ml) and dichloromethane (DCM) (7 ml) at 0° C. was added chloroacetyl chloride (130 ul, 1.64 mmol) and the mixture was stirred at 0° C. for 30 min. Diluted with water, brine and ethyl acetate (EtOAc), separated phases, dried organic layer over sodium sulfate. Removal of the solvent in vacuum left the title compound as an off-white solid (497 mg, 99%), which was used without further purification. MS (ISP): m/z=336.1 [(M+H)+], 338.2 [(M+2+H)+] and 340.1 [(M+4+H)+].

Workup

  1. customseparated phases, dried organic layer over sodium sulfate
  2. customRemoval of the solvent in vacuum
  3. waitleft the title compound as an off-white solid (497 mg, 99%), which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-43a7c05dc34241e4959edd90fb1729fd
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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