Allyl bromide → [4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester

HRID 25118

반응식

HRID 25118 반응식
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C(Br)C=C>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:3][CH:2]=[CH2:1])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester수율 71%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6342Acetonitrile용매2회

실험 절차

Potassium tert-butoxide (1.7 g, 15.2 mmol) and 18-crown-6 (0.1 g, 0.3 mmol) were added to a solution of 29 (4.3 g, 14.3 mmol) in dry MeCN (80 mL) and the mixture was stirred for 20 min at room temperature. After this time, allyl bromide (1.2 mL, 14.3 mmol) in MeCN (10 mL) was added. The reaction mixture was stirred overnight at room temperature, then the precipitate was filtered off and washed with ethyl acetate. The organic fractions were combined, the solvent was removed at reduced pressure and the residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes) to provide compound 30 (3.4 g, 71%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.55 (m, 4H), 2.54 (t, 2H), 3.20 m, 2H), 4.50 (d, 2H), 5.08 (s, 2H), 5.28 (d, 1H), 5.40 (d, 1H), 6.06 (m, 1H), 6.82 (d, 2H), 7.05 (d, 2H), 7.33 (s, 5H).

후처리

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethyl acetate
  4. customthe solvent was removed at reduced pressure
  5. customthe residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b5691c73bf6147188819ae0d3a31163c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858615B2

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