Water → (1R,5S,6S)-6-((1R)-1-Hydroxyethyl)-2-[(3S,5S)-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylic acid

HRID 568219Notes

Reaction equation

HRID 568219 reaction equation
C(OC([N:7]1[C@H:11]([CH:12]([OH:21])[C:13]2[N:14]3[CH:20]=[N:19][CH:18]=[C:15]3[S:16][CH:17]=2)[CH2:10][C@H:9]([S:22][C:23]2[C@H:24]([CH3:40])[C@@H:25]3[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:26]3[C:27]=2[C:28]([O:30]CC=C)=[O:29])[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:38][C@@H:36]([C@H:35]1[C:34](=[O:39])[N:26]2[C:27]([C:28]([OH:30])=[O:29])=[C:23]([S:22][C@H:9]3[CH2:10][C@@H:11]([CH:12]([OH:21])[C:13]4[N:14]5[CH:20]=[N:19][CH:18]=[C:15]5[S:16][CH:17]=4)[NH:7][CH2:8]3)[C@H:24]([CH3:40])[C@H:25]12)[CH3:37]

Participants

6

Reactant 3

HCID 962WaterHCID 7515N-MethylanilineHCID 131722300HCID 131722300, compound

Product 1

HCID 131722299(1R,5S,6S)-6-((1R)-1-Hydroxyethyl)-2-[(3S,5S)-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylic acidYield 20.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (13.8 mg) is added to a solution of 70 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) and 0.077 ml of N-methylaniline in 1.0 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, and the mixture is washed three times with 5 ml of ethyl acetate. The water layer is filtered, followed by concentration under reduced pressure and freeze drying to give a colorless flocculent material. The flocculent material is purified by column chromatography (water-methanol) on Cosmosil 40C18-PREP to give 11.5 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe mixture is washed three times with 5 ml of ethyl acetate
  2. filtrationThe water layer is filtered
  3. concentrationfollowed by concentration under reduced pressure and freeze
  4. customdrying
  5. customto give a colorless flocculent material
  6. customThe flocculent material is purified by column chromatography (water-methanol) on Cosmosil 40C18-PREP

Sources & evidence

ORD record
ord-e31af3a734cd44a69f83eb24f9439626
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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