Sodium Hydroxide → Efavirenz aminoalcohol

HRID 659730

Reaction equation

HRID 659730 reaction equation
[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

Participants

4

Reactant 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

Product 1

HCID 11033574Efavirenz aminoalcohol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
92.5 °C

Procedure

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). 1H NMR (CDCl3) δ 7.54 (s, 1H), 7.12 (dd, J=8.5, 1.5 Hz, 1H), 6.62 (d, J=8.6 Hz, 1H), 4.47 (br. s, 3H), 1.44-1.35 (m, 1H), 0.93-0.88 (m, 2H), 0.83-0.80 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-eaea59cf545c48cd8de85f253727fb29
Source dataset
uspto-grants-2011_12
Patent number
US08080655B2

Linked notes

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