Hydrochloric Acid → HCID 11328213, compound

HRID 493507Notes

Reaction equation

HRID 493507 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:36])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[O:25][C:24]=3[CH2:32][CH2:33][CH2:34][CH3:35])=[O:22])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.O.Cl>C1COCC1>[CH2:32]([C:24]1[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:23]=1[C:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([OH:36])=[O:4])=[CH:9][CH:10]=2)=[CH:19][CH:18]=1)=[O:22])[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131727450HCID 131727450, compound

Product 1

HCID 11328213HCID 11328213, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (721 μL, 0.721 mmol) was added under nitrogen to a solution of methyl[(4′-{[(2-butyl-1-benzofuran-3-yl)carbonyl]amino}[1,1′-biphenyl]-4-yl)oxy]acetate (300 mg, 0.656 mmol), prepared in the previous step, in 30 mL of THF plus 10 mL of water at room temperature. After the addition the reaction was stirred at room temperature for 18 h (overnight). The reaction was acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (188 mg, 65%) as a white solid, mp 225-227° C.; MS (APCI) m/z 444 [M+H]+. Elemental Analysis for C27H25NO5.0.07 H2O: Calc'd: C, 72.92; H, 5.70; N, 3.15; Found: C, 72.45; H, 5.64; N, 3.06

Workup

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. concentrationconcentrated under reduced pressure
  4. customThe solid that formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-6a180b2fec9a455ab158dcd411597f90
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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