Diazomethane → HCID 13591256, compound

HRID 2290421Notes

Reaction equation

HRID 2290421 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([NH:12][C@H:13]1[C:20](=[O:21])[N:19]2[C@@H:14]1[O:15][CH2:16][C:17]([OH:29])=[C:18]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCOCC.C(Cl)Cl>[C:4]([NH:12][C@H:13]1[C:20](=[O:21])[N:19]2[C@@H:14]1[O:15][CH2:16][C:17]([O:29][CH3:3])=[C:18]2[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])(=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 86741068HCID 86741068, compound

Product 1

HCID 13591256HCID 13591256, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solutin of diazomethane in ether was added to a solution of 260 mg (0.72 mmol) of tert.-butyl (6R, 7R)-7-benzoylamino-3-hydroxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate in 3 ml of anhydrous methylene chloride at room temperature until a yellow coloration remained. The solvent and excess diazomethane were then evaporated off in vacuo and the residue was chromatographed on 18 g of silica gel (toluene:ethyl acetate 2:3). 169 mg (62%) of the title compound were obtained as a colorless rigid foam.

Workup

  1. customThe solvent and excess diazomethane were then evaporated off in vacuo
  2. customthe residue was chromatographed on 18 g of silica gel (toluene:ethyl acetate 2:3)

Sources & evidence

ORD record
ord-54b1dc5c2bee4f549385c97c6ffdf0d0
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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