N-Methylaniline → HCID 131722322, compound

HRID 568234Notes

Reaction equation

HRID 568234 reaction equation
C(OC([N:7]1[C@H:11]([CH:12]([OH:21])[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: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>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.CN(C=O)C>[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[S:17][C:16]5=[CH:18][N:19]=[CH:20][N:15]5[CH:14]=4)[NH:7][CH2:8]3)[C@H:24]([CH3:40])[C@H:25]12)[CH3:37]

Participants

5

Reactant 2

HCID 7515N-MethylanilineHCID 131722323HCID 131722323, compound

Product 1

HCID 131722322HCID 131722322, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (8.4 mg) is added to a solution of 40.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) and 0.045 ml of N-methylaniline in 1. 0 ml of DMF, and the mixture is stirred in an argon atmosphere at room temperature for 35 min. DMF is removed by evaporation under reduced pressure, 3 ml of distilled water is added to the residue, and the mixture is extracted three times with 5 ml of ethyl acetate while removing insolubles. The aqueous layer is concentrated under reduced pressure to distil-off ethyl acetate, and the concentrate is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol) to give 3.5 mg of the title compound as a colorless flocculent material.

Workup

  1. customDMF is removed by evaporation under reduced pressure, 3 ml of distilled water
  2. additionis added to the residue
  3. extractionthe mixture is extracted three times with 5 ml of ethyl acetate
  4. customwhile removing insolubles
  5. concentrationThe aqueous layer is concentrated under reduced pressure to distil-off ethyl acetate
  6. customthe concentrate is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol)

Sources & evidence

ORD record
ord-5e283dccd92740fbb51f1f8e8a7c5555
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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