Ethyl Acetate → Allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valinyloxy-methyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate

HRID 2246135노트

반응식

HRID 2246135 반응식
[OH:1][C@@H:2]([C@H:4]1[C:27](=[O:28])[N:6]2[C:7]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][OH:20])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].Cl.CN(C)CCCN=C=NCC.[N+:41]([C:44]1[CH:61]=[CH:60][C:47]([CH2:48][O:49][C:50]([NH:52][C@H:53]([C:57](O)=[O:58])[CH:54]([CH3:56])[CH3:55])=[O:51])=[CH:46][CH:45]=1)([O-:43])=[O:42].C(OCC)(=O)C>CN(C)C(=O)C.CN(C)C1C=CN=CC=1.[Cl-].[Na+].O>[OH:1][C@@H:2]([C@H:4]1[C:27](=[O:28])[N:6]2[C:7]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][O:20][C:57](=[O:58])[C@H:53]([CH:54]([CH3:55])[CH3:56])[NH:52][C:50]([O:49][CH2:48][C:47]3[CH:60]=[CH:61][C:44]([N+:41]([O-:43])=[O:42])=[CH:45][CH:46]=3)=[O:51])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54494215L-Valine, N-[[(4-nitrophenyl)methoxy]carbonyl]-HCID 69471839Allyl (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 131728009Allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valinyloxy-methyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate수율 32.1%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 31374Dimethylacetamide용매HCID 57417360Sodium chloride; water용매

실험 절차

Allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate (970 mg) was dissolved in 10 ml of N,N-dimethylacetamide. 4-Dimethylaminopyridine (281 mg), 441 mg of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, and 681 mg of N-4-nitrobenzyloxycarbonyl-L-valine were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 50 ml of 20% brine and 50 ml of ethyl acetate, followed by separation. The organic layer was dried over magnesium sulfate. The magnesium sulfate was removed by filtration, and the solvent was removed by distillation under the reduced pressure. The crude product was purified by column chromatography on silica gel (ethyl acetate:n-hexane=2:1, and subsequently ethyl acetate:n-hexane=5:1) to give 517 mg of allyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[[(Z)-2-(4-(N-4-nitrobenzyloxycarbonyl-L-valyloxymethyl)thiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate.

후처리

  1. customfollowed by separation
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe magnesium sulfate was removed by filtration
  4. customthe solvent was removed by distillation under the reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (ethyl acetate

출처 및 근거

ORD 기록
ord-d3c2ee265dbd4b6e864f09001d658499
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687490B2

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