Hydrochloric Acid → (R)-2-(4-chloro-2-(2,2,2-trifluoroacetyl)-phenylamino)-2-oxo-1-phenylethyl pivalate

HRID 659720Notes

Reaction equation

HRID 659720 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[C:15]([O:21][C@H:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23](Cl)=[O:24])(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].CN(C)C1C=CC=CC=1.Cl>ClCCl>[C:15]([O:21][C@H:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])=[O:24])(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 109878821-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethanoneHCID 86649875HCID 86649875, compound

Product 1

HCID 50916664(R)-2-(4-chloro-2-(2,2,2-trifluoroacetyl)-phenylamino)-2-oxo-1-phenylethyl pivalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone (2, 5.0 g, 22.4 mmol) was dissolved in dichloromethane (50 mL) and (R)-2-chloro-2-oxo-1-phenylethyl pivalate (8.54 g, 33.5 mmol) was added. To this mixture N,N-dimethylaniline (2.8 mL, 22.4 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane (50 mL), treated with 1N HCl, washed with brine and the organic layer was separated and evaporated to give (R)-2-(4-chloro-2-(2,2,2-trifluoroacetyl)-phenylamino)-2-oxo-1-phenylethyl pivalate (12) as an brown oil.

Workup

  1. washwashed with brine
  2. customthe organic layer was separated
  3. customevaporated

Sources & evidence

ORD record
ord-5d93f906fcb84bcd9141a877bb855a46
Source dataset
uspto-grants-2011_12
Patent number
US08080655B2

Reaction notes

Loading…