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

HRID 341798

반응식

HRID 341798 반응식
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

참가 물질

5

반응물 3

HCID 11776Triphenylphosphine2회HCID 22044Bromobenzyl CyanideHCID 140379073benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 alcaline 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.

후처리

  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

출처 및 근거

ORD 기록
ord-54c6d3f9d91140ed844099c8c0819e8a
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856307

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