Hydrochloric Acid → 155272-11-0

HRID 1081851Notes

Reaction equation

HRID 1081851 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:31]=[CH:30][C:11](/[CH:12]=[CH:13]/[C:14]2[N:22]([CH3:23])[C:21]3[C:20](=[O:24])[N:19]([CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH3:29])[C:16]=3[N:15]=2)=[CH:10][CH:9]=1)=[O:5])C.O.[OH-].[Li+].Cl>O1CCCC1.C(O)C.O>[C:4]([CH2:6][O:7][C:8]1[CH:31]=[CH:30][C:11](/[CH:12]=[CH:13]/[C:14]2[N:22]([CH3:23])[C:21]3[C:20](=[O:24])[N:19]([CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH3:29])[C:16]=3[N:15]=2)=[CH:10][CH:9]=1)([OH:5])=[O:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 6448954Acetic acid, (4-(2-(1,3-diethyl-2,3,6,7-tetrahydro-7-methyl-2,6-dioxo- 1H-purin-8-yl)ethenyl)phenoxy)-, ethyl ester, (E)-

Product 1

HCID 6448955155272-11-0Yield 21.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 180 (200 mg, 0.47 mmol) obtained in Reference Example 119 was dissolved in a mixed solvent of 4 ml of tetrahydrofuran, 4 ml of ethanol, and 2 ml of water. To the solution was added 98 mg (2.34 mmol) of lithium hydroxide monohydrate, and the mixture was stirred at room temperature for one hour. To the reaction solution was added 2N hydrochloric acid, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform/methanol/acetic acid) to give 40 mg (yield 21%) of Compound 181 as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. customfollowed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent:chloroform/methanol/acetic acid)

Sources & evidence

ORD record
ord-b7b22b3fd9b9427f961338c4f340a367
Source dataset
uspto-grants-1996_12
Patent number
US05587378

Reaction notes

Loading…