Dichloromethane → 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl chloride

HRID 546194Notes

Reaction equation

HRID 546194 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13](NC2C=CN(CC(O)=O)N=2)=[O:14])[CH:5]=CC=1S(C)(=O)=O.[C:31]([Cl:36])(=O)[C:32]([Cl:34])=O.C(Cl)[Cl:38]>CN(C)C=O>[CH:26]1([CH2:25][C@H:12]([C:4]2[CH:3]=[CH:2][C:32]([Cl:34])=[C:31]([Cl:36])[CH:5]=2)[C:13]([Cl:38])=[O:14])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 67189335{3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid

Product 1

HCID 866180523-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionic acid (prepared as in PCT WO 2002/046173 A1, Example 3, 375 mg, 1.31 mmol) was dissolved in methylene chloride (20 mL) and N,N-dimethylformamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 753 μL, 1.76 mmol) which produced gas evolution and it was then warmed to 25° C. and stirred for 1 h. After this time, the reaction was concentrated in vacuo to about 5 mL and then another portion of methylene chloride (˜3 mL) was added to produce a roughly 0.16 M solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl chloride which was used.

Workup

  1. customproduced gas evolution and it
  2. concentrationAfter this time, the reaction was concentrated in vacuo to about 5 mL
  3. additionanother portion of methylene chloride (˜3 mL) was added

Sources & evidence

ORD record
ord-2998bba63a774bacb8de1f057eca62d3
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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