Water → N-Fmoc-3-fluoro-L-tyrosine

HRID 1482236ノート

反応式

HRID 1482236 の反応式
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30](ON3C(=O)CCC3=O)=[O:31])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.O>C(=O)([O-])[O-].[Na+].[Na+]>[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30]([NH:1][C@@H:2]([CH2:6][C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=3)[C:3]([OH:5])=[O:4])=[O:31])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 962WaterHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 6433303-Fluoro-L-tyrosine

生成物 1

HCID 89668487N-Fmoc-3-fluoro-L-tyrosine収率 100.3%

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

実験手順

(S)-2-Amino-3-(3-fluoro-4-hydroxyphenyl)propanoic acid (H-Tyr(3-F)-HH, SP449) (7.2 g, 36.2 mmol) was dissolved in a 10% aqueous sodium carbonate solution (250 ml), N-(9-fluorenylmethoxycarbonyloxy)-succinimide (12.2 g, 36.2 mmol) was added and the mixture was stirred at room temperature for 1.5 hours. Water (120 ml) was added to the reaction solution, and the mixture was then washed with 200 ml of diethyl ether twice and with 100 ml of diethyl ether once. The aqueous layer was made acidic (pH=2) by adding a 6 N aqueous HCl solution thereto, and then extracted with 250 ml of ethyl acetate twice and with 200 ml of ethyl acetate once. The resulting ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound (SP450, 15.3 g, 100%).

後処理

  1. additionwas added
  2. washthe mixture was then washed with 200 ml of diethyl ether twice
  3. additionby adding a 6 N aqueous HCl solution
  4. extractionextracted with 250 ml of ethyl acetate twice
  5. dry with materialThe resulting ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-dd12125ec0074acf87bc2a94b40b9814
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

反応ノート

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