1-Hydroxybenzotriazole → HCID 178454208, Verbindung

HRID 491878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491878
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 178454208HCID 178454208, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-21e67cbef7ce46e9870e900935cf2509
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

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