1,3-Bis(trimethylsilyl)urea → Benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate

HRID 2351127노트

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HRID 2351127 반응식
[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:6]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][S:8][C@H:3]12.C[Si](NC(N[Si](C)(C)C)=O)(C)C.Cl.[CH2:45]([O:48][N:49]=[C:50]([C:54]1[N:58]=[C:57]([NH2:59])[S:56][N:55]=1)[C:51](Cl)=[O:52])[CH:46]=[CH2:47].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:45]([O:48][N:49]=[C:50]([C:54]1[N:58]=[C:57]([NH2:59])[S:56][N:55]=1)[C:51]([NH:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:15])=[C:6]([O:9][S:10]([CH3:13])(=[O:11])=[O:12])[CH2:7][S:8][C@H:3]12)=[O:52])[CH:46]=[CH2:47]

참가 물질

7

반응물 4

HCID 875621,3-Bis(trimethylsilyl)ureaHCID 516892Sodium BicarbonateHCID 736584962-Allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochlorideHCID 88528619Benzhydryl 7-amino-3-mesyloxy-3cephem-4-carboxylate

생성물 1

HCID 131716147Benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate수율 92.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of benzhydryl 7-amino-3-mesyloxy-3cephem-4-carboxylate (6.91 g) and bis(trimethylsilyl)-urea (18.4 g) in methylene chloride (69 ml) was added 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (syn isomer) (4.08 g) at -10° C. under stirring and the mixture was stirred at the same temperature for 30 minutes. After the reaction mixture was added to a stirred mixture of water and methylene chloride, the solution was adjusted to pH 7.0 with a saturated aqueous solution of sodium bicarbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate (syn isomer) (8.90 g).

후처리

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-205fbaa6eb344f8d8d8375c9f6f6cc02
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04871730

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