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

HRID 2300772ノート

反応式

HRID 2300772 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-dceffdc4d38944dc903a4b835fa88925
出典データセット
uspto-grants-2002_12
特許番号
US06498165B1

反応ノート

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