Triethylamine → (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-([[pentyloxy]carbonyl]oxy)-2H-azepin-2-one

HRID 2227154노트

반응식

HRID 2227154 반응식
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:10].[C:17]([O:21][C:22]([NH:24][C@H:25]1[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28][NH:27][C:26]1=[O:33])=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([O:21][C:22]([NH:24][C@H:25]1[CH2:31][CH2:30][C@@H:29]([O:32][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:10])[CH2:28][NH:27][C:26]1=[O:33])=[O:23])([CH3:20])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 69489Pentyl chloroformateHCID 11149222(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one

생성물 1

HCID 69978794(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-([[pentyloxy]carbonyl]oxy)-2H-azepin-2-one수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (2 mL, 15 mmol) is added to a solution of pentyl chloroformate (1.8 g, 12.2 mmol), (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one (1.5 g, 6.1 mmol) and 20 mL of CH2Cl2 at 5° C. The reaction mixture is stirred at room temperature overnight. The reaction mixture is then partitioned with water, and the organic layer is dried (Na2SO4), and concentrated by rotary evaporation. The resulting residue is chromatographed (5% EtOAc—CH2Cl2) to give 1.3 g (60%) of (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-([[pentyloxy]carbonyl]oxy)-2H-azepin-2-one as a pale yellow solid: 1H NMR (CDCl3): δ5.90 (d, J=6 Hz, 1H), 5.77 (t, J=6 Hz, 1H), 4.79 (m, 1H), 4.30 (m, 1H), 4.12 (m, 3H), 3.53 (m, 2H), 2.24 (m, 1H), 1.92 (m, 2H), 1.66 (m, 1H), 1.44 (s, 9H), 1.34 (m, 5H), 0.91 (m, 3H).

후처리

  1. customThe reaction mixture is then partitioned with water
  2. dry with materialthe organic layer is dried (Na2SO4)
  3. concentrationconcentrated by rotary evaporation
  4. customThe resulting residue is chromatographed (5% EtOAc—CH2Cl2)

출처 및 근거

ORD 기록
ord-c722e52dd6d84c63ba7a358a88fd45f7
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06413954B1

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