Sodium Iodide → N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-tert-butyldimethylsiloxy-2-(3-formamido4-benzyloxyphenyl)ethylamine

HRID 226281

반응식

HRID 226281 반응식
Br[CH2:2][C@H:3]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([NH:18][CH:19]=[O:20])[CH:5]=1.[OH:29][C@H:30]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH2:41])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(OC(C)C)(=O)C.CS(C)=O>[OH:29][C@H:30]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH:41][CH2:2][C@H:3]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:4]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:6]([NH:18][CH:19]=[O:20])[CH:5]=2)=[CH:35][CH:34]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 100837532-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethylamineHCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethane

생성물 1

HCID 57755062N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-tert-butyldimethylsiloxy-2-(3-formamido4-benzyloxyphenyl)ethylamine수율 100%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 7915Isopropyl Acetate용매

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온도
140 °C

실험 절차

Intermediate 4 (5.0 g, 11 mmol), intermediate 2 (3.5 g, 14 mmol), and dimethylsulfoxide (10 mL) were combined in a 100 mL round bottom flask and stirred to form a homogeneous solution. Potassium carbonate (6.0 g, 43 mmol) and sodium iodide (1.7 g, 11 mmol) were added and the reaction mixture was heated to 140° C. The reaction mixture was maintained at 140° C. for 10 min, then cooled to room temperature and diluted with water (24 mL) and isopropyl acetate (28 mL). The reaction was stirred until all solids dissolved and then transferred to a separatory funnel. The organic layer was washed with water (17 mL) followed by acetate buffer (5% v/v acetic acid, 12% w/v sodium acetate trihydrate in water, 18 ml) followed by sodium bicarbonate solution (5% w/v in water, 17 mL) followed by saturated aqueous sodium chloride (17 mL). The organic layer was dried over sodium sulfate and concentrated to afford intermediate 5 as a brown gelatinous solid (7.0 g, 11 mmol, >99%). m/z: [M+H+] calcd for C38H49N3O4Si 640.4. found 640.6.

후처리

  1. customto form a homogeneous solution
  2. temperatureThe reaction mixture was maintained at 140° C. for 10 min
  3. temperaturecooled to room temperature
  4. stirringThe reaction was stirred until all solids
  5. dissolutiondissolved
  6. customtransferred to a separatory funnel
  7. washThe organic layer was washed with water (17 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-19715f61058041ef894a38de7a6aaa62
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557247B2

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