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Potassium Carbonate → (2S,4R)-4-ethoxy-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid

HRID 1482389
ノート
印刷プレビュー

反応式

HRID 1482389 の反応式
Cl.[CH2:2]([O:4][C@H:5]1[CH2:9][NH:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6]1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].[C:19](=O)([O:35]N1C(=O)CCC1=O)[O:20][CH2:21][CH:22]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2>O1CCOCC1.O>[CH:33]1[C:34]2[CH:22]([CH2:21][O:20][C:19]([N:8]3[CH2:9][C@H:5]([O:4][CH2:2][CH3:3])[CH2:6][C@H:7]3[C:10]([OH:12])=[O:11])=[O:35])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]=2[CH:30]=[CH:31][CH:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 117735645(2S,4R)-4-ethoxypyrrolidine-2-carboxylic acid hydrochloride

生成物 1

HCID 89668655(2S,4R)-4-ethoxy-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid収率 114.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

(2S,4R)-4-Ethoxypyrrolidine-2-carboxylic acid hydrochloride (Compound SP820) (45 g, 230 mmol) was dissolved in a mixture of 1,4-dioxane (500 ml) and water (500 ml), potassium carbonate (79.4 g, 574 mmol) and (9H-fluoren-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate (Fmoc-OSu, 69.8 g, 207 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with diethyl ether, and the aqueous layer was adjusted to pH 3 with an aqueous potassium bisulfate solution and extracted with ethyl acetate. The resulting organic extract was washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to afford (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-ethoxypyrrolidine-2-carboxylic acid (Compound SP813, Fmoc-Hyp(Et)-OH) (90.7 g, 103%).

後処理

  1. additionwere added
  2. washThe reaction solution was washed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. extractionThe resulting organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bfea5d779c8c42cfb00b9015fbf325be
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409952B2

反応ノート

読み込み中…

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