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

HRID 1482389
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HRID 1482389 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water
용매
HCID 312751,4-Dioxane용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bfea5d779c8c42cfb00b9015fbf325be
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409952B2

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