1-Hydroxybenzotriazole → HCID 178454208、化合物

HRID 491878ノート

反応式

HRID 491878 の反応式
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([O:32][C:33]([NH:35][C@H:36]([CH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1)[CH2:37][CH2:38][C:39](O)=[O:40])=[O:34])([CH3:31])([CH3:30])[CH3:29].C1C=CC2N(O)N=NC=2C=1.CNC(N=C=NCC)CCNC>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:12][CH2:13][C@@H:14]([N:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:39](=[O:40])[CH2:38][CH2:37][C@H:36]([NH:35][C:33]([O:32][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:34])[CH:42]2[CH2:43][CH2:44][O:45][CH2:46][CH2:47]2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 230638731,3-Dimethylaminopropyl-3-ethylcarbodiimideHCID 576783374-tert-butoxycarbonylamino-4-(S)-tetrahydro-pyran-4-yl-butyric acidHCID 178525080HCID 178525080、化合物

生成物 1

HCID 178454208HCID 178454208、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To an ice cooled solution of cis-4-(2-benzyloxy-ethylamino)-cyclohexanecarboxylic acid benzyl ester (3 g, 8.2 mmol), 4-tert-butoxycarbonylamino-4-(S)-tetrahydro-pyran-4-yl-butyric acid (2.4 g, 8.4 mmol) (prepared as in Example 35) and HOBT (2.4 g, 10.5 mmol) in CH2Cl2 (100 mL) was added TEA (2.3 mL), followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 2.0 g, 10 mmol). The reaction mixture was allowed to warm to room temperature and then was stirred overnight. EtOAc (200 mL) was added and the resulting mixture washed with citric acid solution, NaHCO3 solution, and aq. NaCl solution. The organic layer was dried with MgSO4. The EtOAc was evaporated to yield a colorless oil. The colorless oil (crude product) was purified by column chromatography (1:1 EtOAc/Hexane) to yield 4-{(2-benzyloxy-ethyl)-[4-tert-butoxycarbonylamino-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-amino}-cis-cyclohexanecarboxylic acid benzyl ester as a residue.

後処理

  1. washthe resulting mixture washed with citric acid solution, NaHCO3 solution, and aq. NaCl solution
  2. dry with materialThe organic layer was dried with MgSO4
  3. customThe EtOAc was evaporated
  4. customto yield a colorless oil
  5. customThe colorless oil (crude product) was purified by column chromatography (1:1 EtOAc/Hexane)

出典と根拠

ORDレコード
ord-21e67cbef7ce46e9870e900935cf2509
出典データセット
uspto-grants-2009_05
特許番号
US07531545B2

反応ノート

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