Lithium hydroxide, monohydrate → N-Boc-5-(2-propen-1-yloxy)-L-norvaline

HRID 1674542

반응식

HRID 1674542 반응식
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11]C(C)C)=[O:10])[CH:2]=[CH2:3].O.[OH-].[Li+]>C1COCC1.O.O>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([OH:11])=[O:10])[CH:2]=[CH2:3]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 21080143isopropyl 5-allyloxy-2(S)-(tert-butoxycarbonylamino)pentanoate

생성물 1

HCID 21080138N-Boc-5-(2-propen-1-yloxy)-L-norvaline

시약·촉매·용매 2

HCID 962Water용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

A mixture of isopropyl 5-allyloxy-2(S)-(tert-butoxycarbonylamino)pentanoate (product of step 26D, 16.1 g, 51.1 mmol) and lithium hydroxide hydrate (4.19 g, 102 mmol) in THF/water (100 mL/20 mL) was stirred at room temperature under nitrogen for 16 hours. The reaction was diluted with water, washed with ether, pH of aqueous fraction adjusted to ˜4, extracted with ether, combined organic fractions washed with saturated NaCl, dried (MgSO4) and evaporated giving 5-allyloxy-2(S)-(tert-butoxycarbonylamino)pentanoic acid as a light yellow syrup: 1H NMR (300 MHz, Chloroform-D) δ 5.89 (ddt, 1H, J=17.4, 10.4, 5.5), 5.25 (dd, 1H, J=17.4, 1.6 Hz), 5.17 (dd, 1H, J=10.4, 1.6 Hz), 4.30 (br d, 1H, J=6.2), 3.96 (dt, 2H, J=5.9, 1.5 Hz), 3.46 (t, 2H, J=5.9 Hz), 1.96-1.86 (m, 1H), 1.85-1.77 (m, 1H), 1.75-1.64 (m, 2H), 1.43 (s, 9H). LCMS m/z 274 (M+H)+.

후처리

  1. washwashed with ether, pH of aqueous fraction
  2. extractionextracted with ether
  3. washwashed with saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-586bebaa16e944adac63f036dc146197
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003604B2

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