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

HRID 1585483

反応式

HRID 1585483 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6bab3beffce4d6296742112544967dd
出典データセット
uspto-grants-1999_08
特許番号
US05939392

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