Sodium Hydroxide → HCID 178488540, compound

HRID 432069Notes

Reaction equation

HRID 432069 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:49])[CH:19]([CH2:25][CH2:26][NH:27][C:28](C3C=CC(OC)=CC=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][C:21]([O:23]C)=[O:22])[C:3]=12.[OH-].[Na+].OS([O-])(=O)=O.[K+].O1[CH2:63][CH2:62][O:61][CH2:60]C1>>[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])[CH:10]([CH3:11])[CH3:12])[N:5]=[C:4]2[NH:14][N:15]=[C:16]([CH2:17][C:18](=[O:49])[CH:19]([CH2:25][CH2:26][N:27]=[C:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:3]3[CH:2]=[CH:63][C:62]([O:61][CH3:60])=[CH:17][CH:16]=3)[CH2:20][C:21]([OH:23])=[O:22])[C:3]=12

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 516920Potassium bisulfateHCID 178500404HCID 178500404, compound

Product 1

HCID 178488540HCID 178488540, compound

Conditions

Temperature
0 °C

Procedure

Compound 19 (1.33 g; 2 mmole) is dissolved in 10 ml dioxane. This solution is cooled to 0° C. and 1 M aqueous NaOH (8.66 ml) is added drop-wise in 5 aliquots over 2.5 hours. After an additional 2 hours at room temperature the solution is adjusted to pH 5 by drop-wise addition of 2 M KHSO4. Precipitated salts are filtered off and washed with dioxane, and the combined filtrates are evaporated. The residue is co-evaporated with ethanol and methanol/CH2Cl2, then purified by silica gel chromatography to yield (20).

Workup

  1. filtrationPrecipitated salts are filtered off
  2. washwashed with dioxane
  3. customthe combined filtrates are evaporated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-12c230cd47cf425ab6b6c325f96baed0
Source dataset
uspto-grants-2003_12
Patent number
US06660845B1

Reaction notes

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