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

HRID 734321

反応式

HRID 734321 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-32171a7d5ee746c5a0b602b6bdb50f56
出典データセット
uspto-grants-2009_09
特許番号
US07592347B2

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