Potassium Carbonate → N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77321

반응식

HRID 77321 반응식
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([CH:31]([CH3:33])[CH3:32])[N:8]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22]C(=O)C)[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([CH:31]([CH3:33])[CH3:32])[N:8]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:3])([CH3:4])[CH3:2]

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 67155272N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

생성물 1

HCID 67155390N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester수율 85%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a solution of N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (0.75 g, 1.53 mmol) in ethanol-water (35 mL-15 mL) is added potassium carbonate (0.422 g, 3.05 mmol), and the reaction is heated to reflux for 16 h. The solvents are removed in vacuo, and the residue is redissolved in water and extracted three times with dichloromethane. The combined organic extracts are washed with sodium bicarbonate and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product is purified by column chromatography (10% hexanes-ethyl acetate) to afford the title compound as a yellow oil (0.58 g, 85% yield).

후처리

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 16 h
  3. customThe solvents are removed in vacuo
  4. dissolutionthe residue is redissolved in water
  5. extractionextracted three times with dichloromethane
  6. washThe combined organic extracts are washed with sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by column chromatography (10% hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-7a774f54f8724fa78ecf6c8d08696d59
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841291B2

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