Dichloromethane → HCID 58563043, compound

HRID 403232Notes

Reaction equation

HRID 403232 reaction equation
[NH2:1][C@@:2]([C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[F:16])([CH3:8])[CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].ClCCl.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C([O-])(O)=O.[Na+].O.[Cl-].[Na+].O.C(OCC)(=O)C>[Br:15][C:13]1[CH:12]=[CH:11][C:10]([F:16])=[C:9]([C@:2]([NH:1][C:22](=[O:23])[CH2:21][Cl:20])([CH3:8])[CH2:3][C:4]([OH:6])([CH3:5])[CH3:7])[CH:14]=1

Participants

8

Reactant 3

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 58563073HCID 58563073, compound

Product 1

HCID 58563043HCID 58563043, 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 (S)-4-amino-4-(5-bromo-2-fluoro-phenyl)-2-methyl-pentan-2-ol (intermediate A14A) (2.22 g; 7.7 mmol) in sat. aqueous NaHCO3-sol. (25 ml) and dichloromethane (DCM) (35 ml) at 0° C. was added chloroacetyl chloride (672 μl, 8.5 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 sulphate. Removal of the solvent in vacuum left the crude product as a colourless oil (3.11 g, 111%), which was used in the next step without further purification. MS (ISP): m/z=366.0 [(M+H)+], 368.0 [(M+2+H)+] and 370.0 [(M+4+H)+].

Workup

  1. customseparated phases, dried organic layer over sodium sulphate
  2. customRemoval of the solvent in vacuum
  3. waitleft the crude product as a colourless oil (3.11 g, 111%), which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-ea06b9bd1014461c9d7e06eae2efb586
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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