Chloroacetyl chloride → HCID 58155316, compound

HRID 1929471Notes

Reaction equation

HRID 1929471 reaction equation
[NH2:1][C:2]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH:5]1[CH2:7][CH2:6]1)[CH2:3][OH:4].C(=O)([O-])O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:2]([NH:1][C:23](=[O:24])[CH2:22][Cl:21])([CH:5]2[CH2:7][CH2:6]2)[CH2:3][OH:4])[CH:13]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 58155345HCID 58155345, compound

Product 1

HCID 58155316HCID 58155316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(RS)-2-Amino-2-(5-bromo-2-fluoro-phenyl)-2-cyclopropyl-ethanol (2.27 g, 8 mmol) was dissolved in a mixture of dichloromethane (85 ml) and a saturated aqueous solution of sodium hydrogen-carbonate (85 ml). The biphasic mixture was then treated with a solution of chloroacetylchloride (0.69 ml, 8.7 mmol) in dichloromethane. The reaction mixture was stirred at room temperature and the progress of the transformation checked by chromatography. After completion, the reaction mixture was diluted with dichloromethane, the organic layer separated and washed with water, then dried over sodium sulfate and evaporated. The (RS)-N-[1-(5-bromo-2-fluoro-phenyl)-1-cyclopropyl-2-hydroxy-ethyl]-2-chloro-acetamide was obtained as a yellow oil (2.73 g, 94.0% of theory). Mass (calculated) C13H14BrClFNO2 [350.614]; (found) [M+H]+=350, [M+2-H]+=352, [M+4-H]+=354.

Workup

  1. customthe organic layer separated
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-da8b01d30a9946bc8e7a772f7c162677
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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