Hydrochloric Acid → HCID 10204236, compound

HRID 1357223Notes

Reaction equation

HRID 1357223 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:35])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][NH:19][C:20]([C:22]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[O:24][C:23]=3[CH3:34])=[O:21])[CH:14]=2)[CH:9]=1.O.Cl>C1COCC1>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]2[O:24][C:23]([CH3:34])=[C:22]([C:20]([NH:19][CH2:18][C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH:9]=[C:8]([O:7][CH2:6][C:5]([OH:35])=[O:4])[CH:17]=[CH:16]4)=[O:21])[CH:26]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69137716HCID 69137716, compound

Product 1

HCID 10204236HCID 10204236, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (514 μL, 0.514 mmol) was added under nitrogen to a solution of [6-({[5-(4-chloro-phenyl)-2-methyl-furan-3-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (239 mg, 0.514 mmol), prepared in the previous step, in 30 mL of THF plus 15 mL of water. After the addition the reaction was stirred at room temperature for 20 h (overnight). 1 N HCl (1 mL) was added and the reaction then concentrated under reduced pressure to remove the THF. The solid present was removed by filtration and dried under reduced pressure to give the title compound (190 mg, 83%) as a tan solid, mp 177-181° C.

Workup

  1. additionAfter the addition the reaction
  2. customthe reaction
  3. concentrationthen concentrated under reduced pressure
  4. customto remove the THF
  5. customThe solid present was removed by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-1f64d48ab4d149fdb931950070fde671
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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