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Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

HRID 615773
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HRID 615773 반응식
Cl.[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]12.C[Si](CC(N)=O)(C)C.[S:34]1[CH:39]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41](O)=[O:42])[S:37][CH2:36][CH2:35]1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.CN(C)C=O>[S:34]1[CH:39]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41]([NH:2][CH:3]2[C:24](=[O:25])[N:5]3[C:6]([C:11]([O:13][CH2:14][C:15]4[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=4)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]23)=[O:42])[S:37][CH2:36][CH2:35]1
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참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 539358522-Methoxyimino-2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acidHCID 703621504-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

생성물 1

HCID 1317120214-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate
수율 89.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (4.06 g.) and trimethylsilylacetamide (9.19 g.) in ethyl acetate (40 ml.) and a solution of 2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 2.2 g.), N,N-dimethylformamide (0.8 g.) and phosphoryl chloride (1.67 g.) in ethyl acetate (24 ml.) were treated in a similar manner to that of Example 19-(1) to give 4-nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.1 g.).

출처 및 근거

ORD 기록
ord-d588a927ef9448bdb1b8ac04eeffe68d
출처 데이터셋
uspto-grants-1985_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04500709

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