Sodium Hydroxide → Efavirenz aminoalcohol

HRID 389412

Reaktionsgleichung

Reaktionsgleichung von HRID 389412
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C([C@@]23C(C)(C)[C@@](C)(CC2)C(=O)O3)=O)=[C:4]([C@@:22]([OH:32])([C:27]#[C:28][CH:29]2[CH2:31][CH2:30]2)[C:23]([F:26])([F:25])[F:24])[CH:3]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C@@:22]([OH:32])([C:27]#[C:28][CH:29]2[CH2:31][CH2:30]2)[C:23]([F:25])([F:26])[F:24])[CH:3]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 50916497(1S,4R)-N-(4-chloro-2-((S)-4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide

Produkt 1

HCID 11033574Efavirenz aminoalcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
92.5 °C

Versuchsvorschrift

A suspension of (1S,4R)-N-(4-chloro-2-((S)-4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide (10, 1 g, 2.13 mmol) and 40% NaOH aqueous solution (20 mL) was stirred at 90-95° C. for 20 hours. Toluene (20 mL) was added and the layers were separated. The organic layer was washed with water (20 mL) and evaporated to dryness to give (S)-4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl) aniline (8).

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with water (20 mL)
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d9ed9a1e8bfd44fe94868be9e6b73c0c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378143B2

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