Hydrogen Bromide → t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

HRID 1463169노트

반응식

HRID 1463169 반응식
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:20]([NH:21][C:22]3[NH:23][C:24]4[CH:30]=[C:29]([CH2:31][NH2:32])[CH:28]=[CH:27][C:25]=4[N:26]=3)[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2].CO[CH:36](OC)[N:37]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(N(CC)CC)C.Br>O1CCOCC1.CO>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:20]([NH:21][C:22]3[NH:23][C:24]4[CH:30]=[C:29]([CH2:31][N:32]=[CH:36][N:37]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)[CH:28]=[CH:27][C:25]=4[N:26]=3)[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 1183521-(Dimethoxymethyl)hexahydro-1H-azepineHCID 70509618t-Butyl 3-acetoxymethyl-7-(5-aminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

생성물 1

HCID 70508669t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

실험 절차

To a solution of t-butyl 3-acetoxymethyl-7-(5-aminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate (93 mg.) in dioxane (2 ml.) and methanol (3 ml.) at 20° was added dimethoxyhexahydro-1H-azepin-1-ylmethane (30 mg.) and then triethylamine. The mixture was cooled to 0° and stirred for 30 minutes. Two equivalents of HBr in methanol were added and the solvent evaporated. The residue was dissolved in the minimum CH2Cl2 and triethylamine hydrobromide precipitated by addition of ether. The product was purified by chromatography on magnesium silicate using CH2Cl2 /MeOH 98:2 v/v as eluant to give t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate having the following n.m.r. in d6DMSO: 1.63 (s, 9H); 1.7 (s, 8H); 2.17 (s, 3H); 3.3-4.0 (br, 6H); 4.67 (s, 2H); 4.75 (d, 1H); 5.1 (d, 1H); 5.38 (d, 1H); 6.0 (d, 1H); 6.8-7.5 (m, 3H); 8.43 (s, 1H).

후처리

  1. temperatureThe mixture was cooled to 0°
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in the minimum CH2Cl2 and triethylamine hydrobromide
  4. customprecipitated by addition of ether
  5. customThe product was purified by chromatography on magnesium silicate

출처 및 근거

ORD 기록
ord-368df7cb7eb640e5b92bb7a84167fc7b
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04463173

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