1,2-Dichloroethane → 1-Benzyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane

HRID 734321

반응식

HRID 734321 반응식
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:28]([CH:25]2[CH2:26][CH2:27][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:23][CH2:24]2)=[O:29])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 2283651-Benzyl-1,4-diazepaneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

생성물 1

HCID 603546031-Benzyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Benzyl-[1,4]-diazepane (3.78 g) and 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (5.0 g) were dissolved in DCM (150 ml) and TEA (3.6 ml) was added followed by HOBT (1.34 g) and finally EDC (4.90 g). The reaction was stirred at rt overnight. The reaction mixture was then evaporated to a minimum, re-dissolved in DCM (50 ml) and washed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml). The organic layer was dried (MgSO4) and evaporated to a crude which was purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]. Fractions containing pure desired product were combined and evaporated to give the subtitled compound as a pale brown solid (7.1 g).

후처리

  1. customThe reaction mixture was then evaporated to a minimum
  2. dissolutionre-dissolved in DCM (50 ml)
  3. washwashed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to a crude which
  6. customwas purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]
  7. additionFractions containing pure desired product
  8. customevaporated

출처 및 근거

ORD 기록
ord-32171a7d5ee746c5a0b602b6bdb50f56
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592347B2

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