Oxalyl chloride → HCID 178465412, compound

HRID 1719912Notes

Reaction equation

HRID 1719912 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 the 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. customis used without purification in the next step

Sources & evidence

ORD record
ord-5a7265c45b55419d870ba7bc3dcba7aa
Source dataset
uspto-grants-1985_09
Patent number
US04543257

Reaction notes

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