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Ethanol → benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate

HRID 906957
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906957
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:28]([CH3:30])[CH3:29])[CH:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:14][C:15](OCC)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C>[Si:21]([O:20][CH:13]([CH2:14][CH2:15][OH:16])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:28]([CH3:30])[CH3:29])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 67390315ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate

Produkt 1

HCID 86640708benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamateAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, to a suspension (303 mL) of ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate (17.7 g), calcium chloride (6.73 g) and sodium borohydride (4.58 g) in dehydrated THF was added with stirring under ice-cooling dehydrated ethanol (152 mL), and the mixture was gradually warmed to room temperature and stirred for 15 hr. The reaction mixture was slowly poured into a mixture of ethyl acetate and ice water (containing 1 mol/L hydrochloric acid, 122 mL) and the mixture was partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1) to give benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate as colorless oil (yield: 14.9 g).

Aufarbeitung

  1. stirringstirred for 15 hr
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1)

Quellen und Nachweise

ORD-Eintrag
ord-2c36faa00f764cba848ee15c192bd6ec
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08013008B2

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