Benzyl glyoxylate → HCID 70592921, compound

HRID 2050401Notes

Reaction equation

HRID 2050401 reaction equation
[N:1]([CH2:4][C@H:5]1[C@@H:8]([NH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:20])[NH:6]1)=[N+]=[N-].[C:21]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])[CH:22]=O>C(O)(=O)C.C(Cl)Cl.[Zn]>[CH2:26]([O:25][C:21](=[O:24])[CH:22]=[N:1][CH2:4][C@H:5]1[C@@H:8]([NH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:20])[NH:6]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 2

HCID 11008258Benzyl glyoxylateHCID 12762157HCID 12762157, compound

Product 1

HCID 70592921HCID 70592921, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

cis-2-Azidomethyl-3-benzyloxycarbonylamino-4-oxoazetidine is treated with zinc dust in 50% aqueous acetic acid as described in Preparation 7. Reaction of the crude reduction product with benzyl glyoxalate in methylene dichloride as described in the procedure of Example 1 gives N-(cis-3-benzyloxycarbonylamino-4-oxo-2-azetidinylmethyl)iminoacetic acid benzyl ester which, when treated with acetyl chloride according to the procedure of Example 1, gives 3-acetyl-6β-benzyloxycarbonylamino-7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester.

Workup

  1. customas described in Preparation 7

Sources & evidence

ORD record
ord-6c6ee2eb977641d2b719d5cfe10376ff
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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