HCID 88542676, Verbindung → HCID 67986476, Verbindung

HRID 219612

Reaktionsgleichung

Reaktionsgleichung von HRID 219612
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20]/[C:21](=[N:28]\[S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH3:35][C:36](=[CH2:40])[CH2:37][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C@@:21]([NH:28][S@@:29]([C:31]([CH3:33])([CH3:32])[CH3:34])=[O:30])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:37][C:36]([CH3:40])=[CH2:35])[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH3:9])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 88542676HCID 88542676, VerbindungHCID 178448200HCID 178448200, Verbindung

Produkt 1

HCID 67986476HCID 67986476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (S)-1-(4-bromophenyl)ethyl((E)-4-((R)-tert-butylsulfinylimino)-4-phenylbutyl)carbamate (1.97 g, 3.59 mmol) in dry THF (60 mL) was cooled to −78° C. A solution of 2-methylallylmagnesium chloride (0.5M in THF, 14.4 mL, 2 equiv) was added slowly. After 2 h, the mixture was warmed to rt and stirred for 1 h. LC-MS found reaction completed. The mixture was quenched with satd aq NH4Cl (10 mL), diluted with ether (100 mL), washed with water (30 mL), brine (25 mL), dried over Na2SO4. Filtration and concentration gave crude tert-butyl (S)-1-(4-bromophenyl)ethyl((S)-4-((R)-1,1-dimethylethylsulfinamido)-6-methyl-4-phenylhept-6-enyl)carbamate (2.30 g) which was used for next steps without further purifications. LC-MS Method 1 tR=2.53 min, m/z 605, 607(M+1).

Aufarbeitung

  1. customreaction
  2. customThe mixture was quenched with satd aq NH4Cl (10 mL)
  3. additiondiluted with ether (100 mL)
  4. washwashed with water (30 mL), brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-c8aff95c99b042608a1ab693a9689c76
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202857B2

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