Sodium Azide → Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate

HRID 970301ノート

反応式

HRID 970301 の反応式
I[CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N+:23]=[N-:24]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 88159309Tert-butyl n-[1-(r/s)-(iodomethyl)undecyl]carbamate

生成物 1

HCID 91612995Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate収率 54%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

tert-Butyl N-[1-(R/S)-(iodomethyl)undecyl]carbamate 62 (250 mg, 0.608 mmol) was dissolved in abs. DMF (10 ml). Sodium azide (79.0 mg, 1.22 mmol) was added to the solution, which was subsequently stirred at 110° C. for 12 hours. Following evaporation, the residue was taken up in CH2Cl2 (50 ml) and was washed with NaHCO3(sat, aq) (1×50 ml). The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography in hexane:ether 10:1 (v/v) to give 63 (100 mg, 54%).

後処理

  1. customevaporation
  2. washwas washed with NaHCO3(sat, aq) (1×50 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography in hexane:ether 10:1 (v/v)

出典と根拠

ORDレコード
ord-d7cd17848bf745a6b01ac0d5450456bf
出典データセット
uspto-grants-2007_12
特許番号
US07312194B2

反応ノート

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