Triphenylphosphine → N-Cbz-4-(aminomethyl)benzamidine

HRID 482257

反応式

HRID 482257 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]([NH:30][C:31]([C:33]1[CH:42]=[CH:41][C:36]([CH2:37][N:38]=[N+]=[N-])=[CH:35][CH:34]=1)=[NH:32])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(C(Br)C1C=CC=CC=1)#N>C1COCC1>[NH2:38][CH2:37][C:36]1[CH:41]=[CH:42][C:33]([C:31](=[NH:32])[NH:30][C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])=[CH:34][CH:35]=1

参加物

5

反応物 3

HCID 11776Triphenylphosphine2 回HCID 22044Bromobenzyl CyanideHCID 140379073benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate2 回

生成物 1

HCID 138391585N-Cbz-4-(aminomethyl)benzamidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

26.3 g (100 mmol) triphenylphosphine was added at room temperature to the 4-(benzyloxycarbonylamidino) benzyl azide from (iii) above dissolved in 160 ml THF. After 16 h an additional 6.6 g (25 mmol) triphenylphosphine was added and the solution was allowed to stand for 4 h before removal of the solvent in vacuo. The residue was dissolved in methylene chloride and extracted with 2M HCl. The aqueous phase was washed with methylene chloride and ether and was subsequently made alkaline with 3.75M sodium hydroxide solution. Extraction with methylene chloride followed by drying (K2CO3) and removal of the solvent in vacuo gave 20 g (The total yield starting from cyanobenzyl bromide is 28%) of a yellow oil which solidified on standing.

後処理

  1. customto stand for 4 h before removal of the solvent in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted with 2M HCl
  4. washThe aqueous phase was washed with methylene chloride and ether
  5. extractionExtraction with methylene chloride
  6. customby drying
  7. custom(K2CO3) and removal of the solvent in vacuo
  8. customgave 20 g (The total
  9. customyield

出典と根拠

ORDレコード
ord-57b25311b4df4b5d847734b63b83c792
出典データセット
uspto-grants-1998_08
特許番号
US05795896

関連ノート

読み込み中…