N-Methylaniline → HCID 131722322, compound

HRID 568235Notes

Reaction equation

HRID 568235 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.C(OCC)(=O)C>ClCCl.CN(C=O)C.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[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

7

Reactant 3

HCID 7515N-MethylanilineHCID 8857Ethyl AcetateHCID 131722323HCID 131722323, compound

Product 1

HCID 131722322HCID 131722322, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (30.7 mg) is added to a solution of 51.6 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 B) described in Example 16-a) and 0.057 ml of N-methylaniline in a mixture of 2.0 ml of dry dichloromethane and 0.5 ml of DMF, and the mixture is stirred in an argon atmosphere at room temperature for 1.5 hr. Ethyl acetate (10 ml) is added thereto, and the resultant precipitate is further washed twice with 5 ml of ethyl acetate and dried in vacuo to give a yellow powder. This powder is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol) to give 0.83 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe resultant precipitate is further washed twice with 5 ml of ethyl acetate
  2. customdried in vacuo
  3. customto give a yellow powder
  4. customThis powder is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol)

Sources & evidence

ORD record
ord-7606705b32654ad58d602834e16d01a1
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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