Water → Ammonia

HRID 1433252노트

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HRID 1433252 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[C@@H:16]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](=[O:35])([O-:34])[O-].[Cs+].[Cs+].[C:38]([O:42][C:43](=[O:53])[NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]Br)([CH3:41])([CH3:40])[CH3:39].O>CN(C)C=O.[Cl-].[Na+].O>[NH3:19].[C:2]([O:34][C:32]([N:44]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([C@@H:16]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:24])[CH3:25])[CH:11]=1)[C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:53])=[O:35])([CH3:7])([CH3:3])[CH3:1]

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonate3회HCID 10108474tert-butyl N-(7-bromoheptyl)carbamate3회HCID 579331854-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

생성물 2

HCID 222AmmoniaHCID 69008693Di-tert-butyl(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)imidodicarbonate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 57417360Sodium chloride; water용매

실험 절차

4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 16, 150 mg, 0.36 mmol) was dissolved in dimethylformamide (2 ml), caesium carbonate (140 mg, 0.43 mmol) was added and stirred at room temperature for 30 minutes. tert-Butyl(7-bromoheptyl)carbamate (Prepared according to J. Med. Chem., 1994, 137, p2537-2551; 170 mg, 0.43 mmol), dissolved in dimethylformamide (1 ml), was added and heated to 70oC. After 2.5 hours caesium carbonate (70 mg, 0.22 mmol) was added and after a further 10 minutes tert-butyl(7-bromoheptyl)carbamate (70 mg, 0.18 mmol) was added. After 1 hour caesium carbonate (20 mg, 0.06 mmol) and tert-butyl(7-bromoheptyl)carbamate (35 mg, 0.09 mmol) were added and after 1 hour at 70° C. the mixture was cooled to room temperature and stirred for 3 days before the addition of water and brine were added, the mixture extracted with ethyl acetate, dried (magnesium sulphate), filtered and the solvents removed in vacuo and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98/2/0.2 to 95/5/0.5 by volume) to furnish the title compound as a colourless gum, 220 mg.

후처리

  1. additionwas added
  2. temperatureheated to 70oC
  3. additionwas added
  4. temperaturewas cooled to room temperature
  5. additionwere added
  6. extractionthe mixture extracted with ethyl acetate
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customthe solvents removed in vacuo
  10. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-34bb0e0b25ff42a18a2d6a8be1db03ff
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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