Hydrochloric Acid → HCID 86600984, compound

HRID 2221165Notes

Reaction equation

HRID 2221165 reaction equation
CO[C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:19]2[O:23][C:22]3[CH:24]=[CH:25][CH:26]=[C:27]([N:28]4[CH2:31][CH2:30][CH2:29]4)[C:21]=3[CH:20]=2)[C:14](=[O:18])[CH:15]=[CH:16][CH3:17])=[CH:6][CH:5]=1.[NH2:33][OH:34].CO.[ClH:37]>C1COCC1.O.[OH-].[Na+]>[ClH:37].[N:28]1([C:27]2[C:21]3[CH:20]=[C:19]([N:13]([C:14](=[O:18])[CH:15]=[CH:16][CH3:17])[CH2:12][CH2:11][O:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([NH:33][OH:34])=[O:32])=[CH:9][CH:8]=4)[O:23][C:22]=3[CH:24]=[CH:25][CH:26]=2)[CH2:29][CH2:30][CH2:31]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 887MethanolHCID 69209072HCID 69209072, compound

Product 1

HCID 86600984HCID 86600984, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-[2-(4-azetidin-1-yl-3-benzofuran-2-yl-but-2-enoylamino)ethoxy]-benzoic acid methyl ester (158 mg, 0.362 mmol) in THF (4 ml), a solution of hydroxylamine in 50% water (2.78 ml) and 1N NaOH (0.1 ml) were added. Methanol was added dropwise until a homogeneous solution was obtained. The reaction mixture was stirred overnight at rt. After cooling the mixture at 0° C., 6 N HCl was added until pH 7 was reached. The solid was separated by filtration and the crude solid purified by HPLC to give the title compound (25 mg) as a white solid.

Workup

  1. customwas obtained
  2. temperatureAfter cooling the mixture at 0° C.
  3. customThe solid was separated by filtration
  4. customthe crude solid purified by HPLC

Sources & evidence

ORD record
ord-a120a2444ceb43889e2a7d6f1430ffec
Source dataset
uspto-grants-2008_05
Patent number
US07368476B2

Reaction notes

Loading…