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

HRID 2261416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261416
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

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 7915Isopropyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ce7c0721498a4dd4aeb7f55d82112343
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846973B2

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