Sodium Hydroxide → HCID 178491592, compound

HRID 488557Notes

Reaction equation

HRID 488557 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:22][CH2:23][CH2:24][N:25]([C:31](=[O:53])[CH2:32][C:33]2[C:41]3[C:36](=[N:37][CH:38]=[N:39][C:40]=3[NH:42][C:43]([C:45]3[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=3)=[O:44])[NH:35][N:34]=2)[CH2:26][C:27]([O:29]C)=[O:28])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:22][CH2:23][CH2:24][N:25]([C:31](=[O:53])[CH2:32][C:33]2[C:41]3[C:36](=[N:37][CH:38]=[N:39][C:40]=3[NH:42][C:43]([C:45]3[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=3)=[O:44])[NH:35][N:34]=2)[CH2:26][C:27]([OH:29])=[O:28])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501607HCID 178501607, compound

Product 1

HCID 178491592HCID 178491592, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound (12) (1.43 g; 2 mmole) is dissolved in dioxane (10 ml). The 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 pH is adjusted to 5 by drop-wise addition of 2M HKSO4. Precipitated salts are filtered off, washed with dioxane, then the combined filtrates are dried in vacuo. The residue (13) is co-evaporated with ethanol and methanol/CH2Cl2, then purified by silica gel chromatography.

Workup

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

Sources & evidence

ORD record
ord-546a288682f244fe88ddbd303e989dd9
Source dataset
uspto-grants-2005_12
Patent number
US06972328B2

Reaction notes

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