Diisopropylethylamine → (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate

HRID 1852200ノート

反応式

HRID 1852200 の反応式
Cl.[NH2:2][CH:3]([C@H:9]([CH2:17]C)[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CCN(C(C)C)C(C)C.[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O>C(Cl)Cl>[C:32]([O:31][C:29]([NH:2][CH:3]([C@H:9]([CH3:17])[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:28])([CH3:35])([CH3:34])[CH3:33]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86683258(3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochloride

生成物 1

HCID 86683235(3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate収率 62.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochloride (2.99 g, 10.77 mmole) in DCM (20 mL) was added DIPEA (1.08 mL, 10.77 mmole) followed by (BOC)2O (2.39 mL, 10.77 mmole) at room temperature. The reaction mass was stirred at room temperature for overnight. The reaction mass was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by column chromotography (Silica gel, 20% ethyl acetate in pet-ether) to get 2.3 g, (62.5%) of (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate as an oily liquid. MS: MS m/z 342.4 (M++1).

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customto get crude compound
  5. customThe crude compound was purified by column chromotography (Silica gel, 20% ethyl acetate in pet-ether)

出典と根拠

ORDレコード
ord-d9771bda81c743d494ff75a4061f774e
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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