Chloroacetyl chloride → HCID 66931584, compound

HRID 1929486Notes

Reaction equation

HRID 1929486 reaction equation
[NH2:1][C@@:2]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH3:7])[C:3]([CH3:6])([OH:5])[CH3:4].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])([CH3:7])[C:3]([OH:5])([CH3:4])[CH3:6])[CH:13]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 58155290HCID 58155290, compound

Product 1

HCID 66931584HCID 66931584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-3-amino-3-(5-bromo-2-fluoro-phenyl)-2-methyl-butan-2-ol (2.91 g, 10.5 mmol) in dichloromethane (35 ml) was stirred intensively together with a saturated sodium hydrogen-carbonate solution (30 ml) at 0° C. Chloroacetyl chloride (0.92 ml, 11.6 ml) was added and stirring continued for 1 hour at 0° C. For the workup, the aqueous layer was separated and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, then evaporated. The title compound was obtained as a white solid (3.5 g, 94% of theory) which was used in the next step without further purification. Mass (calculated) C13H16BrClFNO2 [352.629]; (found) [M+H]+=352, [M+2-H]+=354.

Workup

  1. customFor the workup, the aqueous layer was separated
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-02e46a9b53374e2e8339e3dead91e7c9
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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