Benzyl Alcohol → HCID 178453647, 화합물

HRID 1984939노트

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HRID 1984939 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13](C(O)=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1C=CC=CC=1>[CH2:43]([O:50][C:24](=[O:33])[NH:21][C@H:13]1[CH2:12][CH2:11][C@H:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178453624HCID 178453624, 화합물

생성물 1

HCID 178453647HCID 178453647, 화합물수율 102.2%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
80 °C

실험 절차

To a solution of trans-4-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid (46.9 g, 0.18 mol) in benzene (300 mL) were added triethylamine (24.2 g, 0.24 mol) and diphenylphosphoryl azide (55.9 g, 0.20 mol). The reaction mixture was stirred at 80° C. for 1 hr. To the mixture was added benzyl alcohol (25.9 g, 0.24 mol) and stirred at 100° C. for 4 hr. The mixture was subsequently cooled to ambient temperature for overnight, concentrated, and the resulting pale orange solid dissolved in EtOAc. The organic layer was washed with water (three times), concentrated, and the residue was purified by column chromatography (silica gel, 50% EtOAc in hexane) to give trans-[4-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-carbamic acid benzyl ester (66.7 g, 100%) as a white solid.

후처리

  1. stirringstirred at 100° C. for 4 hr
  2. temperatureThe mixture was subsequently cooled to ambient temperature for overnight
  3. concentrationconcentrated
  4. dissolutionthe resulting pale orange solid dissolved in EtOAc
  5. washThe organic layer was washed with water (three times)
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (silica gel, 50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-1234717ee49b42fdb0b106cc56092bdb
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544690B2

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