L-Homoserine → (2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-4-hydroxybutanoic acid

HRID 62435

反応式

HRID 62435 の反応式
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].C([O-])(O)=O.[Na+].[C:14](ON1C(=O)CCC1=O)([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15].CCOCC.O>O.CC(C)=O>[C:14]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])([O:16][CH2:17][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:15]

参加物

7

反応物 4

HCID 12647L-HomoserineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 21584184Diethylether water

生成物 1

HCID 15449971(2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-4-hydroxybutanoic acid収率 88%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

L-homoserine (15 g, MW119.12, 0.126 mol) and NaHCO3 (22 g, MW84, 0.26 mol) were dissolved in water (600 mL). The solution was chilled in an ice bath, followed by addition of Fmoc-OSu (42.5 g, MW337.3, 0.126 mol) in acetone (400 mL). The mixture was stirred overnight. A mixture of ether/water (200 mL/200 mL) was added, and the solid was filtered off. The filtrate was separated and the aqueous phase was washed with ethyl twice (100 mL×2), followed by acidifying with 3N HClaq (about 100 mL) to pH3-4. The suspension was extracted with ether (200 mL×2). The combined organic phases were washed with brine once (100 mL) and dried over Na2SO4. After evaporation, white solid was obtained (weight: 38 g, yield: 88%).

後処理

  1. temperatureThe solution was chilled in an ice bath
  2. additionwas added
  3. filtrationthe solid was filtered off
  4. customThe filtrate was separated
  5. washthe aqueous phase was washed with ethyl twice (100 mL×2)
  6. extractionThe suspension was extracted with ether (200 mL×2)
  7. washThe combined organic phases were washed with brine once (100 mL)
  8. dry with materialdried over Na2SO4
  9. customAfter evaporation
  10. customwhite solid was obtained (weight: 38 g, yield: 88%)

出典と根拠

ORDレコード
ord-13d45cf8286f4c1b922e0a1388f241ba
出典データセット
uspto-grants-2016_09
特許番号
US09446157B2

関連ノート

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