Sodium Hydroxide → HCID 178454503, compound

HRID 432068Notes

Reaction equation

HRID 432068 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[N:5]=[C:4]2[NH:14][N:15]=[C:16]([CH2:17][C:18]([O:20]C)=[O:19])[C:3]=12.[OH-].[Na+]>O>[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[N:5]=[C:4]2[NH:14][N:15]=[C:16]([CH2:17][C:18]([OH:20])=[O:19])[C:3]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178499648HCID 178499648, compound

Product 1

HCID 178454503HCID 178454503, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 17 (4.41 g; 15 mmole) is suspended in 25 ml water, and a 2N aqueous solution of sodium hydroxide is added drop-wise at 0° C., while maintaining the pH at 11, until the methyl ester is completely hydrolyzed. The reaction solution is then filtered, and the filtrate is brought to pH 3 using 2 M KHSO4 solution, then extracted with ethyl acetate. The aqueous phase is evaporated and the product (18) is purified by chromatography.

Workup

  1. temperaturewhile maintaining the pH at 11
  2. filtrationThe reaction solution is then filtered
  3. extractionextracted with ethyl acetate
  4. customThe aqueous phase is evaporated
  5. customthe product (18) is purified by chromatography

Sources & evidence

ORD record
ord-3b83802465814d818a7ed8cb48973437
Source dataset
uspto-grants-2003_12
Patent number
US06660845B1

Reaction notes

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