HCID 23674932, compound → HCID 86585658, compound

HRID 1358916Notes

Reaction equation

HRID 1358916 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:15]=1Cl)[C@H:11]([NH:17][C:18](=[O:51])[C:19]([C:25]1[N:26]=[C:27]([NH:31][C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[S:28][C:29]=1[Cl:30])=[N:20][O:21][CH2:22][CH2:23][F:24])[C:10]2=[O:52])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:53][C:54]1[S:58][C:57]([S-:59])=[N:56][N:55]=1.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:15]=1[S:59][C:57]1[S:58][C:54]([NH2:53])=[N:55][N:56]=1)[C@H:11]([NH:17][C:18](=[O:51])[C:19]([C:25]1[N:26]=[C:27]([NH:31][C:32]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[S:28][C:29]=1[Cl:30])=[N:20][O:21][CH2:22][CH2:23][F:24])[C:10]2=[O:52])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 23674932HCID 23674932, compoundHCID 86585659HCID 86585659, compound

Product 1

HCID 86585658HCID 86585658, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (7R)-3-chloro-7-[2-[5-chloro-2-(tritylamino)-thiazol-4-yl]-2-(2-fluoroethoxyimino)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid t-butyl ester XV (45 mg, 0.057 mmol) and sodium 5-amino-[1,3,4]thiadiazole-2-thiolate (10 mg, 0.064 mmol) in DMF (0.5 mL) was stirred at room temperature for 3 hr. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure the title compound (8 mg, 16%) was isolated by radial chromatography on silica gel (dichloromethane/methanol 50:1).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporating the solvent under reduced pressure the title compound (8 mg, 16%)
  5. customwas isolated by radial chromatography on silica gel (dichloromethane/methanol 50:1)

Sources & evidence

ORD record
ord-a0bdabc02cb44051af92133ac5168711
Source dataset
uspto-grants-2003_07
Patent number
US06599893B2

Reaction notes

Loading…