Diisopropylethylamine → tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate

HRID 2175230노트

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HRID 2175230 반응식
[C:1](=[O:21])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1.C(N(C(C)C)C(C)C)C.Cl.[NH2:32][CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(Cl)Cl>[Br:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH2:3][O:2][C:1]([NH:32][CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:21]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 867125803-Bromobenzyl 4-nitrophenyl carbonate

생성물 1

HCID 70982800tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate수율 91.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-bromobenzyl 4-nitrophenyl carbonate (8 g, 21.58 mmol) in DCM (50 mL) was added N-ethyl-N-isopropylpropan-2-amine (7.47 mL, 43.2 mmol) and tert-butyl 3-aminopropanoate hydrochloride (3.92 g, 21.58 mmol). Upon the completion of addition, the reaction mixture was stirred at room temperature for 1 h and then quenched with water. The resulting mixture was extracted with CH2Cl2 and the combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (7.10 g, 89% yield) as a light brown oil. LCMS, [M-tBu+2H]+=302.1. 1H NMR (400 MHz, CDCl3) δ 7.50 (s, 1H), 7.44 (d, J=7.7 Hz, 1H), 7.29-7.19 (m, 2H), 5.31 (br. s, 1H), 5.06 (s, 2H), 3.43 (dd, J=12.1, 6.1 Hz, 2H), 2.46 (t, J=6.0 Hz, 2H), 1.45 (s, 9H).

후처리

  1. additionUpon the completion of addition
  2. customquenched with water
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-50% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-106df750ef9540c09fc5760194567fea
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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