Dimethylformamide → HCID 12085190, compound

HRID 1166457Notes

Reaction equation

HRID 1166457 reaction equation
[C:1]1([C@@H:7]([CH3:12])[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:16])=O.CN(C=O)C>CO.C1(C)C=CC=CC=1.[Rh]>[CH:1]1([C@@H:7]([CH3:12])[CH2:8][C:9]([Cl:16])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 852991(3S)-3-phenylbutanoic acid

Product 1

HCID 12085190HCID 12085190, compound

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

(S)-3-phenylbutyric acid was hydrogenated using Rh/C in MeOH at 60 psi and 60° C. for 3.2 hours. The reduced product was then converted to the title acid chloride by treating with 1 eq of oxalyl chloride, and a catalytic amount of DMF, in toluene for 90 minutes, followed by evaporation of the volatile materials.

Workup

  1. customat 60 psi and 60° C.
  2. customfor 3.2 hours
  3. customfollowed by evaporation of the volatile materials

Sources & evidence

ORD record
ord-e425d4f156254adc9d08a4f60024b1b6
Source dataset
uspto-grants-2003_09
Patent number
US06613880B2

Reaction notes

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