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

HRID 1358922ノート

反応式

HRID 1358922 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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): δ 5.90 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-a20e1a541ad448b3a707be7a4db653cc
出典データセット
uspto-grants-2003_07
特許番号
US06599898B2

反応ノート

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