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

HRID 229796노트

반응식

HRID 229796 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

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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 resxulting 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 resxulting 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-659e292adbee42fc808784a739c17ac0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563784B2

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