Acetic Acid → tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate

HRID 1994125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994125
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)C>C1COCC1.C(O)C>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86606495HCID 86606495, Verbindung

Produkt 1

HCID 86606496tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl (2S)-2,3-bis[(tert-butoxycarbonyl)amino]-propanoate (3.57 g, 11.2 mmol) in THF (60 mL) at 0° C. was added lithium chloride (523 mg, 12.3 mmol) and then sodium borohydride (467 mg, 12.3 mmol) portionwise. Ethanol (30 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 18 h. Acetic acid (0.707 mL, 12.3 mmol) was added and the solvents were evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (2.35 g, 72.2%). LCMS: (FA) ES+ 291.2 (M+1).

Aufarbeitung

  1. customthe solvents were evaporated
  2. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1c06efc9f3db4ec1a0d2f702ec34232f
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652041B2

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