Methanol → (3R)-2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoic acid

HRID 1852176ノート

反応式

HRID 1852176 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]([CH3:23])[CH2:16][CH:17]([CH3:22])[CH2:18][CH2:19][CH:20]=[CH2:21])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[Li+].[OH-]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]([CH3:23])[CH2:16][CH:17]([CH3:22])[CH2:18][CH2:19][CH:20]=[CH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86683235(3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate

生成物 1

HCID 86683236(3R)-2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoic acid収率 68%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate (20 g, 0.061 moles) in THF/water (200 mL, 1:1) was added methanol (60 mL) followed by LiOH (7.7 g, 0.183 moles) at room temperature. The reaction mass was stirred at room temperature overnight. The solution was concentrated under reduced pressure and the residue was diluted with water (200 mL). The aqueous solution was acidified with aqueous 1.5 N HCl solution to pH ˜3 and extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduce pressure to get crude compound. The crude compound was purified by column chromotography (Silica gel, 3% methanol in DCM) to get 12.4 g (68%) of (3R)-2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoic acid as gummy liquid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.4 (sb, 1H), 6.92-6.85 (m, 1H), 5.81-5.75 (m, 1H), 5.04-4.93 (m, 2H), 4.12-3.91 (m, 1H), 2.18-1.98 (m, 4H), 1.5 (s, 9H), 1.35-1.02 (m, 3H), 0.98-0.85 (m, 6H).

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe residue was diluted with water (200 mL)
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto get crude compound
  7. customThe crude compound was purified by column chromotography (Silica gel, 3% methanol in DCM)

出典と根拠

ORDレコード
ord-b8e692ad82a1453da96ed3add6c4450f
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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