Hydrochloric Acid → HCID 10278831, compound

HRID 1357224Notes

Reaction equation

HRID 1357224 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:38])[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[C:34]([F:37])([F:36])[F:35])=[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]([C:34]([F:36])([F:35])[F:37])=[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:38])=[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 69137776HCID 69137776, compound

Product 1

HCID 10278831HCID 10278831, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (324 μL, 0.32 mmol) was added under nitrogen to a solution at room temperature of [6-({[5-(4-chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (140 mg, 0.27 mmol), prepared in the previous step, in 15 mL of THF plus 8 mL of water. After the addition the reaction was stirred at room temperature for 7 h. The reaction was acidified with 1 N HCl and then concentrated under reduced pressure to remove the THF. The solid present was collected by filtration and dried under reduced pressure to give the title compound (125 mg, 91%) as an off-white solid, mp 194-196° C.

Workup

  1. additionAfter the addition the reaction
  2. concentrationconcentrated under reduced pressure
  3. customto remove the THF
  4. filtrationThe solid present was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b1dbd440e2fd4b51aef88cf834f16685
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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