Sodium Azide → (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate

HRID 1254216ノート

反応式

HRID 1254216 の反応式
CS(O[CH2:6][C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[N:23]([CH2:6][C@@H:7]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[N+:24]=[N-:25]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 10735550(S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate

生成物 1

HCID 59382971(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

(S)-2-(tert-Butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate (13.3 g, 39.3 mmol) from Step 1 was dissolved in anhydrous DMF (140 mL). Solid NaN3 (5.18 g, 79.7 mmol) was added and the reaction was warmed to 50° C. for 5 h. The reaction mixture was permitted to cool to rt and the solvent was removed under reduced pressure (150 Torr, 55° C.). This material was taken up into Et2O (150 mL), washed with water (3×10 mL) and brine (3×10 mL), dried (Na2SO4), decanted, and stripped to give 13.9 g crude product. This was separated on a silica column using a gradient from 0-100% EtOAc in hexanes. Solvent was stripped from appropriate fractions to give (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate (7.21 g, 65%) as a clear oil. 1H NMR (CDCl3) δ 0.60=1.80 (m 12H), 1.40 (s, 9H), 2.86 (d, 1H), 3.29 (d, 1H), 4.85 (d, 1H), 4.51 (m, 1H), 8.00 (s, 1H). MS ESI +ve m/z 183 (M(−BOC)+1).

後処理

  1. temperatureto cool to rt
  2. customthe solvent was removed under reduced pressure (150 Torr, 55° C.)
  3. washwashed with water (3×10 mL) and brine (3×10 mL)
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. customto give 13.9 g crude product
  7. customThis was separated on a silica column

出典と根拠

ORDレコード
ord-f2ebce1b6dcd45c6a809403ab7f79d59
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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