Water → HCID 131722307, compound

HRID 568225Notes

Reaction equation

HRID 568225 reaction equation
C(OC([N:7]1[C@H:11]([CH2:12][C:13]2[N:20]3[C:16]([S:17][CH:18]=[CH:19]3)=[CH:15][N:14]=2)[CH2:10][C@H:9]([S:21][C:22]2[C@H:23]([CH3:39])[C@@H:24]3[C@@H:34]([C@H:35]([OH:37])[CH3:36])[C:33](=[O:38])[N:25]3[C:26]=2[C:27]([O:29]CC=C)=[O:28])[CH2:8]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>[OH:37][C@@H:35]([C@H:34]1[C:33](=[O:38])[N:25]2[C:26]([C:27]([OH:29])=[O:28])=[C:22]([S:21][C@H:9]3[CH2:10][C@@H:11]([CH2:12][C:13]4[N:20]5[C:16]([S:17][CH:18]=[CH:19]5)=[CH:15][N:14]=4)[NH:7][CH2:8]3)[C@H:23]([CH3:39])[C@H:24]12)[CH3:36]

Participants

6

Reactant 3

HCID 962WaterHCID 7515N-MethylanilineHCID 131722308HCID 131722308, compound

Product 1

HCID 131722307HCID 131722307, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (7.0 mg) is added to a solution of 34.5 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-5-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate and 0.040 ml of N-methylaniline in 1.2 ml of dry dichloromethane in an argon atmosphere at room temperature for 60 min. Distilled water (3 ml) is added thereto, the mixture is washed three times with 6 ml of ethyl acetate, and the aqueous layer is filtered, followed by concentration under reduced pressure and freeze drying to give 16.7 mg of a colorless flocculent material. The colorless flocculent material is purified by column chromatography on Cosmosil 40C18-PREP (water-methanol) to give 9.8 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe mixture is washed three times with 6 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-3d05dcdb02134a06b219af13a52921c9
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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