Oxalyl chloride → HCID 20357837, compound

HRID 2083804Notes

Reaction equation

HRID 2083804 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([NH:12][CH:13]([O:17][CH3:18])[C:14]([O-])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl.N1C=CC=CC=1>[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([NH:12][CH:13]([O:17][CH3:18])[C:14]([Cl:25])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 20357868HCID 20357868, compound

Product 1

HCID 20357837HCID 20357837, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium N-(p-nitrobenzyloxycarbonyl)-α-methoxyglycinate (0.92 g, 3 mMol) is suspended in dry CH2Cl2 (25 ml) and cooled in an ice-water bath. Oxalyl chloride (0.38 g, 3 mMol) and 2 drops of pyridine are added. The resulting mixture is stirred in the cold for 2 hours, and then filtered. The filtrate, which contains N-(p-nitrobenzyloxycarbonyl)-α-methoxyglycyl chloride, is used directly in the next step.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationfiltered

Sources & evidence

ORD record
ord-798d27b4ee8945beb05c97f869b0ee87
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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