Lithium hydroxide, monohydrate → L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-

HRID 1008850ノート

反応式

HRID 1008850 の反応式
[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([O:18]C)=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6].O[Li].O>CO.O>[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([OH:18])=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 59287267L-Valine,3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-,methyl ester

生成物 1

HCID 59287076L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-収率 98%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

A solution (0.1 M) of methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valinate in 2:1 mixture of MeOH/H2O was treated with LiOH.H2O (4 eq) and then heated at 60° C. for 4 h. The mixture was cooled and concentrated to half volume, then diluted with EtOAc and acidified with aqueous HCl (1 N). The organic layer was separated and washed with brine then dried. Removal of the volatiles afforded the title compound (98%) as an oil. MS (ES+) m/z 284 (M+H)+

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to half volume
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customthen dried
  7. customRemoval of the volatiles

出典と根拠

ORDレコード
ord-64d800bbd410487d8bd95329f9bca68a
出典データセット
uspto-grants-2011_07
特許番号
US07973040B2

反応ノート

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