1-Hydroxybenzotriazole → HCID 178454208, 화합물

HRID 491878노트

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HRID 491878 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 178454208HCID 178454208, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-21e67cbef7ce46e9870e900935cf2509
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531545B2

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