Oxalyl chloride → HCID 178465412, compound

HRID 867592Notes

Reaction equation

HRID 867592 reaction equation
[N+:1]([C:4]1[CH:58]=[CH:57][CH:56]=[CH:55][C:5]=1[CH2:6][O:7][C:8]([CH:10]([PH:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[N:11]1[CH:14]([CH2:15][C:16](O)=[O:17])[CH:13]([CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[O:23])[CH3:20])[C:12]1=[O:35])=[O:9])([O-:3])=[O:2].C(Cl)(=O)C([Cl:62])=O>C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:58]=[CH:57][CH:56]=[CH:55][C:5]=1[CH2:6][O:7][C:8]([CH:10]([PH:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[N:11]1[C@@H:14]([CH2:15][C:16]([Cl:62])=[O:17])[C@H:13]([CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[O:23])[CH3:20])[C:12]1=[O:35])=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178465411HCID 178465411, compound

Product 1

HCID 178465412HCID 178465412, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylmethyl)-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(carboxymethyl)-2-azetidinone (0.1320 g from the previous step) is dissolved in 5 ml CH2Cl2 and cooled to 0° under N2. Oxalyl chloride (0.040 ml, 0.44 mmole) is added dropwise over 5 minutes and then 1 drop of DMF is added. The mixture is stirred at 0° for 5 minutes and then at 25° C. for another 15 minutes. The solvent and excess oxalyl chloride are evaporated under reduced pressure. The residue is then desired acid chloride which is used without purification in the next step.

Workup

  1. temperaturecooled to 0° under N2
  2. waitat 25° C. for another 15 minutes
  3. customThe solvent and excess oxalyl chloride are evaporated under reduced pressure
  4. customdesired acid chloride which is used without purification in the next step

Sources & evidence

ORD record
ord-4870b7c336c14dd9a815ada757ae8356
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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