Potassium Carbonate → benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-(thiadiazol-5-ylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 992716Notes

Reaction equation

HRID 992716 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:8](O)=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].CS(Cl)(=O)=O.[NH2:43][C@@H:44]1[C:73](=[O:74])[N:46]2[C:47]([C:57]([O:59][CH:60]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[O:58])=[C:48]([S:51][C:52]3[S:56][N:55]=[N:54][CH:53]=3)[CH2:49][S:50][C@H:45]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>CN(C)C(=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)/[C:8]([NH:43][C@@H:44]2[C:73](=[O:74])[N:46]3[C:47]([C:57]([O:59][CH:60]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)=[O:58])=[C:48]([S:51][C:52]4[S:56][N:55]=[N:54][CH:53]=4)[CH2:49][S:50][C@H:45]23)=[O:9])[N:6]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 10117176(Z)-2-(2-Aminothiazol-4-yl)-2-((trityloxy)imino)acetic acidHCID 11708267BistrimethylsilylacetamidHCID 70122870Diphenylmethyl 7beta-amino-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate

Product 1

HCID 88180013benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-(thiadiazol-5-ylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 81.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of 2-(2-aminothiazol-4-yl)-2-(Z)-trityloxyiminoacetic acid (2.87 g) in N,N-dimethylacetamide (28.7 ml) was added potassium carbonate (0.925 g) and methanesulfonyl chloride (1.04 ml) under ice-cooling. After stirring at the same temperature for 30 minutes, the mixture was added dropwise to a solution of diphenylmethyl 7β-amino-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (3.23 g) and bis-trimethylsilylacetamide (9.93 ml) in N,N-dimethylacetamide (32.3 ml) under ice-cooling. After being stirred at the same temperature for 45 minutes, the mixture was poured into a mixture of ice-water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to give diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (4.87 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter being stirred at the same temperature for 45 minutes
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d84319cce1344f3392a96602b07df9c5
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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