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

HRID 568240Notes

Reaction equation

HRID 568240 reaction equation
C(OC([N:7]1[C@H:11]([CH2:12][C:13]2[S:17][C:16]3=[CH:18][N:19]=[CH:20][N:15]3[CH: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.C(OCC)(=O)C>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[S:17][C:16]5=[CH:18][N:19]=[CH:20][N:15]5[CH:14]=4)[NH:7][CH2:8]3)[C@H:23]([CH3:39])[C@H:24]12)[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 8857Ethyl AcetateHCID 131722333HCID 131722333, compound

Product 1

HCID 131722332(1R,5S,6S)-6-((1R)-1-Hydroxyethyl)-2-[(3S,5S)-5-(imidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylic acidYield 16.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (16.4 mg) is added to a solution of 81.1 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate and 0.092 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) and 10 ml of ethyl acetate are added thereto remove insolubles. The aqueous layer is washed twice with 3 ml of ethyl acetate and concentrated under reduced pressure, and the concentrate is freeze dried to give a yellow flocculent material which is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol) to give 10.3 mg of the title compound as a colorless flocculent material.

Workup

  1. washThe aqueous layer is washed twice with 3 ml of ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customdried
  4. customto give a yellow flocculent material which
  5. customis then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol)

Sources & evidence

ORD record
ord-5e18796579cc48fc806ec80f01bf9ab6
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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