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Sodium hydride → HCID 117871199, 화합물

HRID 627026
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HRID 627026 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])(=O)=O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]([CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[C@@H:12]([CH3:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 736104N-carbobenzyloxyalanineHCID 184645972-(Methylsulfonyl)ethyl methanesulfonate

생성물 1

HCID 117871199HCID 117871199, 화합물수율 41.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a 100 mL round-bottomed flask, (S)-2-(benzyloxycarbonylamino)propanoic acid (331 mg, 1.48 mmol, Eq: 1.00) was combined with THF (9 mL) to give a colorless solution. Sodium hydride (131 mg, 3.26 mmol, Eq: 2.2) was added. The reaction was stirred at rt for 30 min, then 2-(methylsulfonyl)ethyl methanesulfonate (300 mg, 1.48 mmol, Eq: 1.00) was added and the reaction was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine then dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 10% to 60% EtOAc in hexanes) to give (S)-2-[benzyloxycarbonyl-(2-methanesulfonyl-ethyl)-amino]-propionic acid (201 mg).

후처리

  1. customto give a colorless solution
  2. stirringthe reaction was stirred at rt overnight
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 40 g, 10% to 60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-38185ec196f44befa7d7885b6a987231
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309248B2

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