Methanol → HCID 131722315, compound

HRID 568229Notes

Reaction equation

HRID 568229 reaction equation
N1CCOCC1.C(OC([N:13]1[C@H:17]([CH:18]([OH:27])[C:19]2[N:26]3[C:22]([S:23][CH:24]=[CH:25]3)=[CH:21][N:20]=2)[CH2:16][C@H:15]([S:28][C:29]2[C@H:30]([CH3:46])[C@@H:31]3[C@@H:41]([C@H:42]([OH:44])[CH3:43])[C:40](=[O:45])[N:32]3[C:33]=2[C:34]([O:36]CC=C)=[O:35])[CH2:14]1)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>C1COCC1.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.ClCCl.C(OCC)(=O)C>[OH:44][C@@H:42]([C@H:41]1[C:40](=[O:45])[N:32]2[C:33]([C:34]([OH:36])=[O:35])=[C:29]([S:28][C@H:15]3[CH2:16][C@@H:17]([CH:18]([OH:27])[C:19]4[N:26]5[C:22]([S:23][CH:24]=[CH:25]5)=[CH:21][N:20]=4)[NH:13][CH2:14]3)[C@H:30]([CH3:46])[C@H:31]12)[CH3:43]

Participants

9

Reactant 4

HCID 887MethanolHCID 8083MorpholineHCID 11776TriphenylphosphineHCID 131722313HCID 131722313, compound

Product 1

HCID 131722315HCID 131722315, compoundYield 93.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Morpholine (0.026 ml) and 6.5 mg of tetrakis(triphenylphosphine)palladium(0) are added to a solution of 65.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-5-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) and 12 mg of triphenylphosphine in a mixture of 0.55 ml of anhydrous THF with 0.55 ml of dry methanol, and the mixture is stirred in an argon atmosphere at room temperature for 30 min. Ethyl acetate (5 ml) and 1 ml of dichloromethane are added thereof, and the resultant precipitate is further washed with 5 ml of ethyl acetate and 1 ml of dichloromethane, followed by drying in vacuo to give 48.4 mg of a colorless powder. The colorless powder is successively purified by column chromatography on Cosmosil 40C18-PREP (water:methanol=5:1 to 3:1) and on Cosmosil 5C18-MS (water:methanol=3:1) to give 3.3 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe resultant precipitate is further washed with 5 ml of ethyl acetate and 1 ml of dichloromethane
  2. customby drying in vacuo

Sources & evidence

ORD record
ord-1b723d38afdf46b7a970ba2a3e66cddb
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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