Triethylamine → (R)-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-carbamic acid 4-nitro-phenyl ester

HRID 1243221노트

반응식

HRID 1243221 반응식
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C@H:8]([NH2:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:22]>ClCCl>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([O:23][C:21](=[O:22])[NH:10][C@H:8]([CH3:9])[CH2:7][O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:12])[CH3:11])=[CH:29][CH:28]=1)([O-:32])=[O:31]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 22867570(R)-1-((tert-butyldimethylsilyl)oxy)propan-2-amine

생성물 1

HCID 58715060(R)-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-carbamic acid 4-nitro-phenyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethylamine (693 mg, 3,66 mmol) (from Example 38a supra) and triethylamine (0.77 mL, 5.5 mmol) (Allied Signal) in dichloromethane was treated with 4-nitrophenyl chloroformate (885 mg, 4.39 mmol) (Aldrich) at room temperature for 30 minutes. The reaction was quenched with 1 N aqueous hydrochloric acid and then extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution followed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (15% ethyl acetate in hexanes) to give (R)-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-carbamic acid 4-nitro-phenyl ester as a colorless oil that solidified upon standing. (Yield 0.49 g, 38%).

후처리

  1. customThe reaction was quenched with 1 N aqueous hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography (15% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-564bd44fffe64c0497b4b6a6764abf67
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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