Triphenylphosphine → Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

HRID 1790612

반응식

HRID 1790612 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]([N:30]1[CH2:36][CH:35]([OH:37])[CH:34]([N:38]=[N+]=[N-])[CH2:33][CH2:32][CH:31]1[CH3:41])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O.C1(C)C=CC=CC=1>[CH2:20]([O:27][C:28]([N:30]1[CH2:36][CH:35]([OH:37])[CH:34]([NH2:38])[CH2:33][CH2:32][CH:31]1[CH3:41])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

6

반응물 2

HCID 11776TriphenylphosphineHCID 21036431Racemic (2R,5S,6S)-5-Azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

생성물 1

HCID 21036430Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

Triphenylphosphine (1.94 g, 7.4 mmol) was added to a solution of racemic (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (1.5 g, 4.93 mmol) in THF (185 ml) and H2O (0.7 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotroped in vacuo by rotary evaporation twice. The resulting oil was dissolved in MeOH and HCl in Et2O and the resulting salt was collected following filtration and was used in the next reaction without further purification (1.4 g, 90%).

후처리

  1. customovernight
  2. customwas azeotroped in vacuo by rotary evaporation twice
  3. dissolutionThe resulting oil was dissolved in MeOH
  4. customHCl in Et2O and the resulting salt was collected
  5. filtrationfiltration
  6. customwas used in the next reaction without further purification (1.4 g, 90%)

출처 및 근거

ORD 기록
ord-43e157a4e81d43778d62ce7ac6bb9e65
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071184B2

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