Diethyl Ether → Potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382632

반응식

HRID 382632 반응식
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:19]([O:21]CC=C)=[O:20])=[C:8]([C:11]3[N:18]4[C:14]([S:15][CH:16]=[CH:17]4)=[CH:13][N:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[K+:56].C(OCC)C>ClCCl.C(OCC)(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:19]([O-:21])=[O:20])=[C:8]([C:11]3[N:18]4[C:14]([S:15][CH:16]=[CH:17]4)=[CH:13][N:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[K+:56]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 23669619Potassium 2-ethylhexanoateHCID 131722906allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 131722907Potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate수율 32.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 40 mg of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 0.8 ml of dichloromethane and 0.8 ml of ethyl acetate were added under the atmosphere of argon 3.4 mg of triphenylphosphine, 29 mg of potassium 2-ethylhexanoate, 6.4 mg of tetrakis-triphenylphosphine palladium (0), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into diethyl ether, and the resulting precipitate was collected by filtration, and purified by column chromatography on COSMOSEAL 40C18-PREP (water:methanol=20:1) to give 13 mg of the title compound.

후처리

  1. filtrationthe resulting precipitate was collected by filtration
  2. custompurified by column chromatography on COSMOSEAL 40C18-PREP (water:methanol=20:1)

출처 및 근거

ORD 기록
ord-cb7a875e6e844d3d895021ba1491707b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310056B1

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