Water → HCID 178445234, compound

HRID 1388479Notes

Reaction equation

HRID 1388479 reaction equation
O.[CH2:2]([O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH2:19])[S:17][CH:18]=1)[C:11]([OH:13])=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].P(Cl)(Cl)(Cl)=O.[NH2:25][CH:26]1[C:43](=[O:44])[N:28]2[C:29]([C:40]([OH:42])=[O:41])=[C:30]([CH2:33][S:34][C:35]3[NH:39][N:38]=[N:37][CH:36]=3)[CH2:31][S:32][C@H:27]12>O1CCCC1.C[Si](CC(N)=O)(C)C.CN(C)C=O>[CH2:2]([O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH2:19])[S:17][CH:18]=1)[C:11]([NH:25][CH:26]1[C:43](=[O:44])[N:28]2[C:29]([C:40]([OH:42])=[O:41])=[C:30]([CH2:33][S:34][C:35]3[NH:39][N:38]=[N:37][CH:36]=3)[CH2:31][S:32][C@H:27]12)=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychloride2×HCID 540705992-(2-Aminothiazol-4-yl)-2-n-hexyloxyiminoacetic acidHCID 178508102HCID 178508102, compound

Product 1

HCID 178445234HCID 178445234, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 357676Acetamide, 2-(trimethylsilyl)-Solvent2×

Procedure

Water (0.1 ml) was added to a suspension of 2-hexyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer)(2.0 g) in tetrahydrofuran (20 ml). Phosphorus oxychloride (1.4 g) was added thereto at 0° to 5° C. and the mixture was stirred for 20 minutes at the same temperature. Trimethylsilylacetamide (1.3 g) was added thereto, the mixture was stirred for 20 minutes at the same temperature, phosphorus oxychloride (1.4 g) was added thereto, the resulting mixture was stirred for 20 minutes at 0° to 5° C., dimethylformamide (0.75 g) was added thereto and the resulting mixture was stirred for 1 hour at the same temperature. The resulting solution was at a time added at -20° C. to a solution of 7-amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (3.3 g) in a mixture of tetrahydrofuran (30 ml) and trimethylsilylacetamide (6.8 g). The resulting mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was post-treated according to similar manners to those of the aforementioned Examples to give 7-[2-hexyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.5 g).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred for 20 minutes at 0° to 5° C.
  3. stirringthe resulting mixture was stirred for 1 hour at the same temperature
  4. stirringThe resulting mixture was stirred for 1.5 hours at the same temperature
  5. additionThe reaction mixture was post-treated

Sources & evidence

ORD record
ord-c06174fc4ef34dc49906d5e9f99ddb4b
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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