Hydrogen Bromide → HCID 14180633, compound

HRID 649295Notes

Reaction equation

HRID 649295 reaction equation
[CH:1]1([N:7]([CH3:36])[C:8](=[O:35])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[N:17]([CH2:27][C:28]([O:30][C:31](C)(C)[CH3:32])=[O:29])[CH2:16]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br>C(OCC)(=O)C.C(O)C.C(O)(=O)C>[CH:1]1([N:7]([CH3:36])[C:8](=[O:35])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[N:17]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:16]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 14181855HCID 14181855, compound

Product 1

HCID 14180633HCID 14180633, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-cyclohexyl-N-methyl-4-[2-acetamido-3-tert-butyloxycarbonylmethyl-3,4-dihydroquinazolin-6-yl]oxybutyramide (13.7 g, 25 mmol) was dissolved in a mixture of ethyl acetate and ethanol (10 mL each), and to the mixture was added saturated HBr in acetic acid. After stirring overnight, the mixture was concentrated, dissolved in ethyl acetate and the organic layer was washed with half-saturated sodium bicarbonate and brine, otherwise dried, filtered and evaporated. Column chromatography over silica gel (3:1 dichloromethane-ethyl acetate) afforded the title compound as an amorphous foam which crystalled from cold ether, mp 96°-7° C.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washthe organic layer was washed with half-saturated sodium bicarbonate and brine
  4. customotherwise dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-723b277458a54cf7b395aec2eaf32636
Source dataset
uspto-grants-1988_04
Patent number
US04739056

Reaction notes

Loading…