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

HRID 1852200노트

반응식

HRID 1852200 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d9771bda81c743d494ff75a4061f774e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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