Pyridine → HCID 86742288, compound

HRID 845843Notes

Reaction equation

HRID 845843 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(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].[C:39](Cl)(=[O:42])[CH2:40]C.[I-].[Na+].N1C=CC=C[CH:47]=1>ClCCl>[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][C:47]([C:39](=[O:42])[CH3:40])=[CH:18][N:17]=2)[C:7]=1[C:23]([O:25][CH:26]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5238Sodium IodideHCID 62324Propionyl chlorideHCID 86742286HCID 86742286, compound

Product 1

HCID 86742288HCID 86742288, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 585 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, 127 mg of propionyl chloride, 188 mg of sodium iodide and 15 ml of acetontrile was stirred for 90 minutes, then 99 mg of pyridine was added. This mixture was stirred for 90 minutes, then dichloromethane was added and the mixture was refluxed for 20 minutes. The solution was washed with 10% hydrochloric acid, brine and aqueous sodium bicarbonate, dried and evaporated, giving 418 mg of the desired product.

Workup

  1. stirringThis mixture was stirred for 90 minutes
  2. temperaturethe mixture was refluxed for 20 minutes
  3. washThe solution was washed with 10% hydrochloric acid, brine and aqueous sodium bicarbonate
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-bae1927034414325848860f814d8e625
Source dataset
uspto-grants-1988_07
Patent number
US04760140

Reaction notes

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