1,1'-(Diazomethylene)bis(benzene) → (6R,7R)-7-amino-3-[(7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-2-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

HRID 359625Notes

Reaction equation

HRID 359625 reaction equation
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1[S:26][C:19]3=[N:20][C:21]([CH3:25])=[CH:22][C:23](=[O:24])[N:18]3[N:17]=1)=[C:7]2[C:11]([OH:13])=[O:12].[C:27]1([C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N+]=[N-])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[C:27]1([CH:33]([O:12][C:11]([C:7]2[N:8]3[C@H:3]([S:4][CH2:5][C:6]=2[CH2:14][S:15][C:16]2[S:26][C:19]4=[N:20][C:21]([CH3:25])=[CH:22][C:23](=[O:24])[N:18]4[N:17]=2)[C@H:2]([NH2:1])[C:9]3=[O:10])=[O:13])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 14124717(6R,7R)-7-amino-3-[(7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-2-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 14124719(6R,7R)-7-amino-3-[(7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-2-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl esterYield 42.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of the product obtained in Step 1 (4.9 g) in acetone (40 ml) was added diphenyldiazomethane (8.2 g), and the mixture was stirred overnight at room temperature. After filtering off the insoluble matters, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 2.94 g of the objective compound as yellow crystals.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-23ce84fe2ff843b2be274220c1ba961f
Source dataset
uspto-grants-1991_03
Patent number
US05001121

Reaction notes

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