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

HRID 500377

反応式

HRID 500377 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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, 1.6Hz), 5.17 (dd, 1H, J=10.4, 1.6Hz), 4.30 (br d, 1H, J=6.2), 3.96 (dt, 2H, J=5.9, 1.5Hz), 3.46 (t, 2H, J=5.9Hz), 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)+.

後処理

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

出典と根拠

ORDレコード
ord-e01924e076b24527a69a756e7876c992
出典データセット
uspto-grants-2010_08
特許番号
US07772183B2

関連ノート

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