Acetic acid, 2-(2-naphthalenylthio)- → (Z)-(6R,7R)-3-(3-acetoxy-propenyl)-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1370680Notes

Reaction equation

HRID 1370680 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:12][C:13]([OH:15])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:28]([O:31][CH2:32][CH:33]=[CH:34][C:35]1[CH2:42][S:41][C@H:40]2[N:37]([C:38](=[O:44])[C@H:39]2[NH2:43])[C:36]=1[C:45]([OH:47])=[O:46])(=[O:30])[CH3:29]>CN(C)C(=O)C.C(OCC)(=O)C>[C:28]([O:31][CH2:32]/[CH:33]=[CH:34]\[C:35]1[CH2:42][S:41][C@H:40]2[N:37]([C:38](=[O:44])[C@H:39]2[NH:43][C:13](=[O:15])[CH2:12][S:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:36]=1[C:45]([OH:47])=[O:46])(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 66728Acetic acid, 2-(2-naphthalenylthio)-HCID 682631,1'-CarbonyldiimidazoleHCID 59071335(6R,7R)-3-(3-acetoxy-propenyl)-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 70032403(Z)-(6R,7R)-3-(3-acetoxy-propenyl)-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 58%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 10.5 g (48 mmol) of naphthalen-2-ylsulfanyl-acetic acid in 80 ml of N,N-dimethylacetamide were added 7.8 g (48 mmol) of 1,1′-carbonyldiimidazole and the reaction mixture was stirred for 0.5 h at 20° under an atmosphere of argon. To the yellow solution were added 11.93 g (0.5 mmol) of (Z and E)-(6R,7R)-3-(3-acetoxy-propenyl)-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and stirring was continued for 3 h at 20°. The brown solution was diluted with ethyl acetate (0.5 1), washed with 1 N hydrochloric acid (0.2 1) and with water (5×0.1 1), dried over sodium sulfate and evaporated in vacuo. The remaining material was crystallized from ethyl acetate to give 11.7 g (58%) of (Z)-(6R,7R)-3-(3-acetoxy-propenyl)-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a light brown solid.

Workup

  1. stirringstirring
  2. waitwas continued for 3 h at 20°
  3. washwashed with 1 N hydrochloric acid (0.2 1) and with water (5×0.1 1)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe remaining material was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-134602b1ad234e4ab2922912bbb0d16a
Source dataset
uspto-grants-2003_06
Patent number
US06583133B1

Reaction notes

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