Water → HCID 178462322, compound

HRID 568224Notes

Reaction equation

HRID 568224 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].C(OC([N:12]1[C@H:16]([CH:17]([OH:27])[C:18]2[N+:19]3[C:20](=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:21][CH:22]=2)[CH2:15][C@H:14]([S:28][C:29]2[C@H:30]([CH3:46])[C@@H:31]3[C@@H:41]([C@H:42]([OH:44])[CH3:43])[C:40](=[O:45])[N:32]3[C:33]=2[C:34]([O:36]CC=C)=[O:35])[CH2:13]1)=O)C=C.CNC1C=CC=CC=1.O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[OH:44][C@@H:42]([C@H:41]1[C:40](=[O:45])[N:32]2[C:33]([C:34]([OH:36])=[O:35])=[C:29]([S:28][C@H:14]3[CH2:15][C@@H:16]([CH:17]([OH:27])[C:18]4[N+:19]5[C:20](=[CH:23][N:24]([CH3:26])[CH:25]=5)[S:21][CH:22]=4)[NH:12][CH2:13]3)[C@H:30]([CH3:46])[C@H:31]12)[CH3:43]

Participants

6

Reactant 3

HCID 962WaterHCID 7515N-MethylanilineHCID 178459473HCID 178459473, compound

Product 1

HCID 178462322HCID 178462322, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (18.1 mg) is added to a solution of 55 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate perchlorate (stereoisomer B) and 0.051 ml of N-methylaniline in 0.7 ml of dry dichloromethane, and the mixture is stirred in an argon atmosphere at room temperature for 45 min. Distilled water (3 ml) is added thereto, the mixture is washed three times with 3 ml of ethyl acetate, and the aqueous layer is filtered, followed by concentration under reduced pressure and freeze drying to give 31 mg of a light orange flocculent material. The light orange flocculent material is purified by column chromatography on Cosmosil 5C18-MS (water:methanol=10:1) to give 3.9 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe mixture is washed three times with 3 ml of ethyl acetate
  2. filtrationthe aqueous layer is filtered
  3. concentrationfollowed by concentration under reduced pressure and freeze
  4. customdrying

Sources & evidence

ORD record
ord-87b122fba11346c08fe63d6a369404ae
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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