Oxalyl chloride → HCID 11369167, compound

HRID 1970086Notes

Reaction equation

HRID 1970086 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([O:14][C:15]([N:17]1C[CH2:23][CH2:22][C@@H:18]1C(O)=O)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:4][C:2]([C@H:1]1[CH2:23][CH2:22][CH2:18][N:17]1[C:15]([O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate

Product 1

HCID 11369167HCID 11369167, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture composed of 40 mL of toluene and 40 mL of oxalyl chloride was added—in 30 minutes at room temperature—to a solution of 100 g of 1-[(benzyloxy)carbonyl]-D-proline in 200 mL of toluene and 0.5 mL of DMF. After stirring for 2 hours at 20-25° C. the HPLC showed complete conversion and the reaction mixture was concentrated with oil at about 40° C. under vacuum, redissolved to toluene and reconcentrated obtaining 122.1 g of residue. At 20-25° C. the residue was dissolved in 100.00 mL of THF and this solution was used in example 2.

Workup

  1. concentrationthe reaction mixture was concentrated with oil at about 40° C. under vacuum
  2. dissolutionredissolved to toluene

Sources & evidence

ORD record
ord-f34a2f8a732a4a72b8204b02fa4d8f4f
Source dataset
uspto-grants-2013_04
Patent number
US08426612B2

Reaction notes

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