Water → (1S)-2-azido-1-phenylethanamine

HRID 474414노트

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HRID 474414 반응식
CS(O[CH2:6][C@@H:7]([NH:14]C(OC(C)(C)C)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)=O.[N-:22]=[N+:23]=[N-:24].[Na+].O>CN(C=O)C>[N:22]([CH2:6][C@@H:7]([NH2:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[N+:23]=[N-:24]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 10335849(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate

생성물 1

HCID 10953837(1S)-2-azido-1-phenylethanamine수율 135.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

To a solution of (2S)-2-[(tert-Butoxycabonyl)amino]-2-phenylethyl methanesulfonate (ref. Org. Syn. 2008, 85, 219) (5.0 g, 15.9 mmol) in DMF (40 mL) was added solid sodium azide (2.2 g, 33 mmol). The reaction was heated to 65° C. for 48 h. The reaction was cooled to room temperature and water was added to provide a white precipitate. The precipitate was filtered and dried under vacuum to afford the desired compound (3.5 g, 85%). To a solution of azide (0.75 g, 2.86 mmol) in THF (14 mL) was added HCl (as a 4M solution in dioxane, 7 mL, 28 mmol). The reaction was stirred at RT for 16 hours, then solvents were removed under reduced pressure to give the amine hydrochloride, which was used in the next step without further purification.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customto provide a white precipitate
  3. filtrationThe precipitate was filtered
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-df5aec282bb34b75b4d24265b45b6985
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637532B2

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