Hydrochloric Acid → HCID 67926517, compound

HRID 981257Notes

Reaction equation

HRID 981257 reaction equation
[C:1]([C:4]1[CH:44]=[CH:43][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([S:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:42])[CH:35]([CH3:41])[CH2:36][C:37]([O:39]C)=[O:38])=[CH:30][CH:29]=3)[CH:20]([CH3:26])[CH2:21][C:22]([O:24]C)=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:45][CH2:46][CH3:47])[C:5]=1[OH:48])(=[O:3])[CH3:2].CO.[OH-].[Na+].Cl>C1COCC1.O>[OH2:3].[C:1]([C:4]1[CH:44]=[CH:43][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([S:27][C:28]3[CH:29]=[CH:30][C:31]([C:34](=[O:42])[CH:35]([CH3:41])[CH2:36][C:37]([OH:39])=[O:38])=[CH:32][CH:33]=3)[CH:20]([CH3:26])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:45][CH2:46][CH3:47])[C:5]=1[OH:48])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 20071763HCID 20071763, compound

Product 1

HCID 67926517HCID 67926517, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester from Step A of this Example (760 mg) in THF (15 ml) and MeOH (1 ml) was added 2N NaOH (2.4 ml) and stirred overnight at room temperature. The reaction mixture was diluted with H2O (50 ml) and acidified with 2N HCl and extracted with CH2Cl2 (2×50 ml). The combined organic layers were washed with brine, dried over Na2SO4 and purified on a column of flash silica gel 230-400 mesh using toluene-dioxane-acetic acid (10:2:0.1) as eluant to give the title compound as a foam (580 mg, 79%).

Workup

  1. extractionextracted with CH2Cl2 (2×50 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. custompurified on a column of flash silica gel 230-400 mesh

Sources & evidence

ORD record
ord-3e4ff46650eb4d4c93f9ead754d97bb9
Source dataset
uspto-grants-1991_02
Patent number
US04990526

Reaction notes

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