Oxalyl chloride → HCID 53833103, compound

HRID 867587Notes

Reaction equation

HRID 867587 reaction equation
[N+:1]([C:4]1[CH:42]=[CH:41][CH:40]=[CH:39][C:5]=1[CH2:6][O:7][C:8]([CH2:10][P:11]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:12]1[CH:15]([CH2:16][C:17](O)=[O:18])[CH2:14][C:13]1=[O:20])=[O:9])([O-:3])=[O:2].C(Cl)(=O)C([Cl:46])=O>C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:42]=[CH:41][CH:40]=[CH:39][C:5]=1[CH2:6][O:7][C:8]([CH2:10][P:11]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:12]1[CH:15]([CH2:16][C:17]([Cl:46])=[O:18])[CH2:14][C:13]1=[O:20])=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 53696852HCID 53696852, compound

Product 1

HCID 53833103HCID 53833103, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

From Step A, 1-(o-nitrobenzyloxycarbonylmethyltriphenylphosphoranyl)-4-(carboxymethyl)-2-azetidinone (0.851 g) is dissolved in 20 ml CH2Cl2 and cooled to 0° C. under N2. Oxalyl chloride (0.8 ml) is added dropwise over 5 min and then 1 drop of DMF is added. The mixture is stirred at 0° C. for 5 min and then at 25° C. for 15 min. The solvent and excess oxalyl chloride are evaporated under reduced pressure. The residue is the desired acid chloride which is used without purification in the next step.

Workup

  1. waitat 25° C. for 15 min
  2. customThe solvent and excess oxalyl chloride are evaporated under reduced pressure
  3. customis used without purification in the next step

Sources & evidence

ORD record
ord-761aa04ee2024925957c923e6d2154b5
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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