(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine → HCID 178431686, Verbindung

HRID 339888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339888
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11](OC)=[N:10][S:9]2(=[O:19])=[O:18])=[CH:4][CH:3]=1.[Si:21]([O:28][CH2:29][CH2:30][C@H:31]([NH2:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:39][C@H:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])[CH2:30][CH2:29][O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])=[N:10][S:9]2(=[O:18])=[O:19])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 68292582(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamineHCID 683592305-(4-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Produkt 1

HCID 178431686HCID 178431686, VerbindungAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 70 mg of 5-(4-bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 66 mg of (S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine in 1 ml of methylene chloride was stirred under a gentle argon stream, such that the solvent evaporated gradually. After stirring at room temperature overnight, the residue was dissolved in 20 ml of dichloromethane and extracted with 10 ml of 0.5 N aqueous hydrochloric acid and 10 ml of water. The organic phase was dried using a phase separator cartridge (Chromabond® PTS), concentrated by rotary evaporation and dried under high vacuum. This gave the product (113 mg) with a molecular weight of 613.7 g/mol (C27H38BrFN2O4SSi); MS (ESI): m/e=614 (M+H+).

Aufarbeitung

  1. customevaporated gradually
  2. dissolutionthe residue was dissolved in 20 ml of dichloromethane
  3. extractionextracted with 10 ml of 0.5 N aqueous hydrochloric acid and 10 ml of water
  4. customThe organic phase was dried
  5. concentrationconcentrated by rotary evaporation
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-61f70af82755484388efcd466590957a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895547B2

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