Oxalyl chloride → HCID 20638812, compound

HRID 1276512Notes

Reaction equation

HRID 1276512 reaction equation
[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13]([OH:15])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:19])=O>C(Cl)Cl.CN(C=O)C>[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13]([Cl:19])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 12633598HCID 12633598, compound

Product 1

HCID 20638812HCID 20638812, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 155 mg (1.02 mmol) of 1(R)-phenyl-2(S)-carboxy cyclohex-5-ene (See U.S. Pat. No. 5,750,549, Example 158, Step B) in 3 mL of CH2Cl2 at 0° C. was added oxalyl chloride (100 uL) followed by DMF (1 drop). The reaction was allowed to warm to room temperature. After stirring 1 hour the reaction was concentrated in vacuo, redissolved in CH2Cl2 and concentrated to a yellow solid which was used directly in the next step.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2
  3. concentrationconcentrated to a yellow solid which

Sources & evidence

ORD record
ord-c6c599b1de474d5ea996d4f4c4155529
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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