(2R,3S)-N-(tert-Butyloxy)carbonyl-3-amino-2-acetoxy-4-phenylbutanal → (2S,3R,4S)-N-[(tert-Butyloxy)carbonyl]-2-amino-1-phenyl-3,4-dihydroxy-6-methylheptane

HRID 21613

Reaktionsgleichung

Reaktionsgleichung von HRID 21613
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:10]([O:13]C(=O)C)[CH:11]=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([Mg]Cl)[CH:25]([CH3:27])[CH3:26]>C1COCC1.CCOCC.CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:10]([OH:13])[C@@H:11]([OH:12])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 2

HCID 14856784(2R,3S)-N-(tert-Butyloxy)carbonyl-3-amino-2-acetoxy-4-phenylbutanalHCID 178418368HCID 178418368, Verbindung

Produkt 1

HCID 10711995(2S,3R,4S)-N-[(tert-Butyloxy)carbonyl]-2-amino-1-phenyl-3,4-dihydroxy-6-methylheptane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

The oil prepared in Example 2 was dissolved under nitrogen in 100 mL of dry THF and cooled to -70°. To this solution was added 13 mL (26 mmol) of a 2. OM solution of isobutylmagnesium chloride in ether and the stirred mixture was allowed to warm to room temperature and stir for 2 hrs. After decomposition with MeOH/H2O the mixture was diluted with ether, washed with saturated NH4Cl solution twice, then dried and the solvents stripped off under vacuum. The residue was allowed to stand overnight in 80% MeOH--H2O containing excess ammonium hydroxide. The MeOH was stripped off and the mixture was extracted with ether. These extracts were combined, washed with water, dilute KHSO4, then dried and evaporated to give 2.36 g of a yellow glass which crystallized from 50 mL of pentane on standing overnight. The yellow-white powder obtained was recrystallized from ether-hexane and furnished the title compound (0.41 g) as white, hairy needles, mp 134°-136° , Rf (ether): single spot, 0.6. By chromatography of the mother liquors and crystallization of the appropriate fractions, an additional 0.22 g of product, mp 138°-139° was obtained.

Aufarbeitung

  1. temperaturecooled to -70°
  2. washwashed with saturated NH4Cl solution twice
  3. customdried
  4. waitto stand overnight in 80% MeOH
  5. extractionthe mixture was extracted with ether
  6. washwashed with water, dilute KHSO4
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ba1c7bac4ab8455887a5545b24865432
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424307

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