Triethylamine → (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one

HRID 1267834노트

반응식

HRID 1267834 반응식
C(N(CC)CC)C.[CH:8]1([C:14](Cl)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[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:14]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:15])[CH2:28][NH:27][C:26]1=[O:33])=[O:23])([CH3:20])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 11149222(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one

생성물 1

HCID 11810372(3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one수율 99.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (8.4 mL, 60 mmol) is added to a solution of cyclohexanecarbonyl chloride (6.3 g, 43.0 mmol), (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one (7.0 g, 28.7mmol) and 100 mL of CH2Cl2 at 50° C. The reaction mixture is stirred at room temp. overnight. The reaction mixture is then partitioned with water, and the organic layer is dried (Na2SO4), and concentrated with rotary evaporation. The resulting residue is chromatographed (5% EtOAc—CH2Cl2) to give 10.1 g (99.5% of (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one as a white solid: 1H NMR (CDCl3): δ 5.89 (d, J=5.27 Hz, 1H), 5.65 (t, J=4.90 Hz, 1H), 4.89 (s, 1H), 4.30 (q, J=4.14 Hz, 1H), 3.49 (m, 2H), 2.31 (tt, J=10.92 Hz and 3.39 Hz, 1H), 2.13 (d, J=14.32 Hz, 1H), 1.98 (d, J=13.56 Hz, 2H), 1.88 (d, J=14.31 Hz, 2H), 1.75 (d, J=11.30 Hz, 2H), 1.66 (s, 2H), 1.45 (s, 9H), 1.30 (m, 5H).

후처리

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

출처 및 근거

ORD 기록
ord-3a42a6d8989f4e739a76f064aebd18b7
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555533B2

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