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

HRID 578650ノート

反応式

HRID 578650 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 10953837(1S)-2-azido-1-phenylethanamine収率 135.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-865ce8b216894af8b11ab50f2183f5a1
出典データセット
uspto-grants-2015_05
特許番号
US09040560B2

反応ノート

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