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Dimethylformamide → 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate

HRID 544037
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HRID 544037 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:10]([OH:12])=O)[N:8]=1)=[O:2].[NH2:20][CH:21]1[C:41](=[O:42])[N:23]2[C:24]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])=[CH:25][CH2:26][S:27][C@H:22]12.CN(C)C=O.P(Cl)(Cl)(Cl)=O>O.CC(C)=O.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:10]([NH:20][CH:21]2[C:41](=[O:42])[N:23]3[C:24]([C:28]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=4)=[O:29])=[CH:25][CH2:26][S:27][C@H:22]23)=[O:12])[N:8]=1)=[O:2]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 538074782-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetic acid

생성물 1

HCID 1317124744-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate수율 100.2%

시약·촉매·용매

3
HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetic acid (syn isomer, 4.14 g.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (4.5 g.), N,N-dimethylformamide (1.41 g.), phosphoryl chloride (2.96 g.), tetrahydrofuran (72 ml.), acetone (15 ml.) and water (15 ml.) were treated in a similar manner to that of Example 15-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 8.1 g.).

출처 및 근거

ORD 기록
ord-5b83dda17632405b9c3450f9064609df
출처 데이터셋
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04447430

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