Methanol → HCID 88199116, compound

HRID 619239Notes

Reaction equation

HRID 619239 reaction equation
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH:9]=[CH2:10])[CH2:7][S:8][C@H:3]12.C[Si](C)(C)NC(=O)C.[NH2:24][C:25]1[S:26][C:27]([Cl:39])=[C:28](/[C:30](=[N:34]/[O:35]C(=O)C)/[C:31](Cl)=[O:32])[N:29]=1.CO>ClCCl>[NH2:24][C:25]1[S:26][C:27]([Cl:39])=[C:28](/[C:30](=[N:34]/[OH:35])/[C:31]([NH:1][C@@H:2]2[C:14](=[O:15])[N:4]3[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH:9]=[CH2:10])[CH2:7][S:8][C@H:3]23)=[O:32])[N:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25989Acetamide, N-(trimethylsilyl)-HCID 7280824(6R,7R)-7-Amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 22118566HCID 22118566, compound

Product 1

HCID 88199116HCID 88199116, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7β-amino-3-vinyl-3-cephem-4-carboxylic acid (1 g) and N-(trimethylsilyl)acetamide (5.8 g) in dichloromethane (10 ml) was added 2-(2-amino-5-chlorothiazol-4-yl)-2-(Z)-(acetoxyimino) acetyl chloride (1.69 g) under ice-cooling. After being stirred at the same temperature for 1 hour, to this mixture was added methanol (10 ml). After evaporating in vacuo to remove the dichloromethane, the residue was added conc. hydrochloric acid (1.95 ml) at room temperature. After being stirred at the same temperature for 4 hours, the mixture was poured into water (10 ml). The mixture was adjusted to pH 3.5 with 28% ammonium hydroxide in water, and the resulting precipitate was collected by filtration to afford 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (137 mg).

Workup

  1. temperaturecooling
  2. customAfter evaporating in vacuo
  3. customto remove the dichloromethane
  4. additionthe residue was added conc. hydrochloric acid (1.95 ml) at room temperature
  5. stirringAfter being stirred at the same temperature for 4 hours
  6. additionthe mixture was poured into water (10 ml)
  7. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-2c9848e7c51541a48c8465f4993b24b0
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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