Sodium borohydride → methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719342
[BH4-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:17]([CH2:18][CH:19]=[O:20])[N:16]([C:21](=[C:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])[C:15]1=[O:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:17]([CH2:18][CH2:19][OH:20])[N:16]([C:21](=[C:26]([CH3:27])[CH3:28])[C:22]([O:24][CH3:25])=[O:23])[C:15]1=[O:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 54489122methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate

Produkt 1

HCID 54247464methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoateAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (10 mg) was added to a solution of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate (49 mg) in methanol (1 ml) at 0° C. The mixture was stirred at the same temperature for 20 minutes and quenched with acetic acid (~0.05 ml). The resulting solution was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with brine containing sodium bicarbonate. The extract was dried over magnesium sulfate, evaporated, and chromatographed on silica gel (1.5 g, eluting with 5-10% acetone in dichloromethane) to give 39 mg of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate.

Aufarbeitung

  1. customquenched with acetic acid (~0.05 ml)
  2. customThe resulting solution was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with brine
  5. additioncontaining sodium bicarbonate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated
  8. customchromatographed on silica gel (1.5 g, eluting with 5-10% acetone in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d99d9711469648e1bfd909b0bf4394e9
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539152

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