Hydrochloric Acid → HCID 178441514, compound

HRID 1464346Notes

Reaction equation

HRID 1464346 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:33])[C:12]2[C:7](=[C:8](OC(=O)CCCC)[CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl.C[OH:43]>[OH-].[Na+]>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:33])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:43])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178447450HCID 178447450, compound

Product 1

HCID 178441514HCID 178441514, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-butyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-8-valeryloxy-4(3H)-quinazolinone (0.3 g) in methanol (5 ml) and 1N sodium hydroxide (2 ml) was stirred at room temperature for 1 hour. After addition of 1N hydrochloric acid, the reaction solution was extracted with ethyl acetate and the organic layer was washed with water, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel to give a crystalline product. Recrystallization from ethyl acetate-ether gave colorless crystals (0.2 g, 80%), mp 212°-214° C.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel
  6. customto give a crystalline product
  7. customRecrystallization from ethyl acetate-ether

Sources & evidence

ORD record
ord-e7f8838f54f04b6ea425ea3fca601e75
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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