Pyridine → HCID 86742289, compound

HRID 845846Notes

Reaction equation

HRID 845846 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:22])[C@H:10]2[NH:14][C:15]([N:17]=[CH:18][N:19](C)C)=[S:16])[C:7]=1[C:23]([O:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2].NOS(O)(=O)=O.N1C=CC=CC=1.O1CCOCC1>C(O)C.CO>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:22])[C@H:10]2[NH:14][C:15]2[S:16][N:19]=[CH:18][N:17]=2)[C:7]=1[C:23]([O:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 76284hydroxylamine-O-sulfonic acidHCID 86742286HCID 86742286, compound

Product 1

HCID 86742289HCID 86742289, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 60 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[[[[(dimethylamino)methylene]amino]thioxomethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester, 14 mg of hydroxylamine-O-sulfonic acid and 17.14 mg of pyridine in a mixture of 3 ml of ethanol and 1 ml of methanol was stirred at room temperature. A 0.5 ml portion dioxane was added to enhance solubility. After 1 hour the mixture was concentrated, dichloromethane added to the residue, the solution washed with 10% hydrochloric acid and brine, then decolorized, filtered and evaporated, giving the desired product.

Workup

  1. concentrationAfter 1 hour the mixture was concentrated
  2. additiondichloromethane added to the residue
  3. washthe solution washed with 10% hydrochloric acid and brine
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cd6ee15305a0486eaa7ae430d6a4df80
Source dataset
uspto-grants-1988_07
Patent number
US04760140

Reaction notes

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