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

HRID 1610800

반응식

HRID 1610800 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

반응 조건

온도
65 °C

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 roomtemperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3 M 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. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organic layer was washed twice with 0.3 M KHSO4 and once with brine
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-1aa582c3a4cc4ab0a7f765ae600bc7f6
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984627B1

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