Sodium Carbonate → Methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate

HRID 1515349

반응식

HRID 1515349 반응식
[NH2:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[C:27](=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[CH2:20]([O:19][C:17](=[O:18])[CH2:27][NH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2회HCID 57425932Methyl 4-aminoadamantane-1-carboxylate

생성물 1

HCID 68520083Methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-aminoadamantane-1-carboxylate obtained in Reference Example 11 (1.87 g) in tetrahydrofuran (20 ml), water (10 ml), benzyl chloroformate (1.53 g) and sodium carbonate (1.13 g) were added and stirred at room temperature for 5 hours. Benzyl chloroformate (0.76 g) was further added and stirred at room temperature for 2 hours. After insoluble materials were filtered off, the solvent was concentrated and the residue was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1) to give methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate (3.30 g) as a colorless powder.

후처리

  1. additionwere added
  2. stirringstirred at room temperature for 2 hours
  3. filtrationAfter insoluble materials were filtered off
  4. concentrationthe solvent was concentrated
  5. extractionthe residue was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customto remove the desiccant
  9. distillationby distilling off the solvent under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1)

출처 및 근거

ORD 기록
ord-8912306657ff4f32a49c1ff8bdc8eddc
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222417B2

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