Ethyl Acetate → 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine

HRID 1975459ノート

反応式

HRID 1975459 の反応式
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:28]=[N+]=[N-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10][NH2:28])=[O:6])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 190992922-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane

生成物 1

HCID 190993162-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine収率 202.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 7.00 g of 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane and 1.42 g of ammonium chloride in 70 ml of N,N-dimethylformamide was added 1.73 g of sodium azide at 0° C. The mixture was stirred at 50° C. for 7 hours. After the starting material disappeared, 350 ml of ethyl acetate and 350 ml of water were added to the reaction mixture. The organic layer was washed in turn with water three times and brine. The half amount of solvent was evaporated and then 5.11 g of triphenylphosphine was added thereto portionwise. After stirring overnight, 2.15 g of 28% aqueous ammonia was added and the mixture was stirred for 8 hours, and then evaporated under reduced pressure to give 11.36 g of crude 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine.

後処理

  1. washThe organic layer was washed in turn with water three times and brine
  2. customThe half amount of solvent was evaporated
  3. addition5.11 g of triphenylphosphine was added
  4. stirringAfter stirring overnight
  5. addition2.15 g of 28% aqueous ammonia was added
  6. stirringthe mixture was stirred for 8 hours
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-be3f58fd5d2448d9b1fe5f886841c916
出典データセット
uspto-grants-1994_02
特許番号
US05286721

反応ノート

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