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Lithium Hydroxide → 2-(2-(((Benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoic acid

HRID 627579
ノート
印刷プレビュー

反応式

HRID 627579 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]#[CH:27])[C:13]([NH:15][CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([O:19]C)=[O:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]#[CH:27])[C:13]([NH:15][CH:16]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:17]([OH:19])=[O:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 78106115Methyl 2-(2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoate

生成物 1

HCID 781061162-(2-(((Benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoic acid収率 84.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of compound 3 (10.85 g; 29 mmol) in dry THF (100 mL) kept in an ice bath was treated with a solution of 1M lithium hydroxide (100 mL) and stirred for 4 h at 0° C. until the starting material disappeared (as shown by TLC). The solvent was removed and the residue was diluted with water (25 mL). The pH of the aqueous solution was adjusted to ˜2 with 5% HCl and the solution was extracted with ethyl acetate (2×250 mL) and washed with brine (100 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated, yielding a crude product which was purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50) to give 4 as a white solid (8.8 g; 84% yield). 1H NMR (DMSO-d6) δ 8.1 (s, 1H), 7.5 (s, 1H), 7.3 (m, 5H), 5.0 (s, 2H), 4.4 (m, 1H), 4.2 (m, 1H), 2.8 (s, 1H), 2.5 (m, 1H), 2.4 (m, 1H), 1.6 (m, 2H), 1.4 (m, 1H), 0.8 (d, 6H)

後処理

  1. customThe solvent was removed
  2. additionthe residue was diluted with water (25 mL)
  3. extractionthe solution was extracted with ethyl acetate (2×250 mL)
  4. washwashed with brine (100 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customyielding a crude product which
  10. customwas purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50)

出典と根拠

ORDレコード
ord-1879fe675820486ab6c7a59ac35662dc
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309284B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート