Water → (S)-1-(3-Tert-butyloxycarbonylphenyl)-1-azidoethane

HRID 2300772노트

반응식

HRID 2300772 반응식
CS(O[C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=1)[CH3:7])(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].O>CN(C)C=O>[C:17]([O:16][C:14]([C:10]1[CH:9]=[C:8]([C@@H:6]([N:21]=[N+:22]=[N-:23])[CH3:7])[CH:13]=[CH:12][CH:11]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 86758754(R)-1-(3-Tert-butyloxycarbonylphenyl)ethylmethanesulfonyl Ether

생성물 1

HCID 86758755(S)-1-(3-Tert-butyloxycarbonylphenyl)-1-azidoethane수율 94.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(R)-1-(3-tert-butyloxycarbonylphenyl)-ethyl methanesulfonyl ether (3.28 mmol) was dissolved in N,N-dimethylformamide (20 mL) and sodium azide (8.57 mmol) was added. The resultant mixture was heated to 60° C. for 45 min then stirred at room temperature overnight. Worked up by pouring into water and extracting 3× with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to yield 769 mg of an oil which was used without further purification. 1H NMR (500 MHz, CDCl3): δ 7.96 (m, 2H); 7.52 (m, 1H); 7.45 (m, 1H); 4.69 (q, J=6.9 Hz, 1H): 1.63 (s, 9H); 1.57 (d, J=6.8 Hz, 3H).

후처리

  1. extractionextracting 3× with diethyl ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dceffdc4d38944dc903a4b835fa88925
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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