Sodium Hydroxide → HCID 58582759, compound

HRID 1611419Notes

Reaction equation

HRID 1611419 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([O:23][CH2:24][CH3:25])[C:18]([O:20]CC)=[O:19])=[CH:12][CH:11]=2)[C:5]([C:26]2C=CC=CC=2C)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:26][C:5]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C@H:17]([O:23][CH2:24][CH3:25])[C:18]([OH:20])=[O:19])=[CH:14][CH:15]=2)[C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86590011HCID 86590011, compound

Product 1

HCID 58582759HCID 58582759, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of substituted ester (prepared in example 2) (1.38 g), sodium hydroxide (3.0%, 15 mL) in methanol (20 mL) was stirred at 20° C. to 25° C. for 10 h. Methanol was evaporated under reduced pressure. The residue was diluted with water (20 mL) and was acidified with dilute hydrochloric acid. The product was extracted with ethyl acetate (3×20 mL) and washed with water (2×80 mL), brine (80 mL) and was dried over sodium sulfate to obtain an oily product (1.2 g, 94%). The crude product (3 g) was separated by column chromatography using silica gel using hexane:ethyl acetate (9:1) as an eluent to afford the pure title compound (0.75 g, 59%).

Workup

  1. customMethanol was evaporated under reduced pressure
  2. additionThe residue was diluted with water (20 mL)
  3. extractionThe product was extracted with ethyl acetate (3×20 mL)
  4. washwashed with water (2×80 mL), brine (80 mL)
  5. dry with materialwas dried over sodium sulfate

Sources & evidence

ORD record
ord-6e647b3720ea423aaa8751159e71b127
Source dataset
uspto-grants-2006_01
Patent number
US06987123B2

Reaction notes

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