Tert-butyl (piperidin-4-ylmethyl)carbamate → benzyl N-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]piperidine-1-carboximidoyl]carbamate

HRID 858

반응식

HRID 858 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:27](=[NH:30])[NH:26][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

생성물 1

HCID 140391597benzyl N-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]piperidine-1-carboximidoyl]carbamate수율 37%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60°-70° C. for six hours and left at room temperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3M KHSO4 and once with brine. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using a stepwise gradient of CH2Cl2 /MeOH (100/0, 97/3, 95/5, 90/10) as eluent to yield 5.22 g (37%) of the title product.

후처리

  1. temperatureThe mixture was heated at 60°-70° C. for six hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washThe organic layer was washed twice with 0.3M KHSO4 and once with brine
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-0b5d6ed5aa3144caa92cff165e2d40f8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723444

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