Hydrochloric Acid → 2-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid

HRID 1357307Notes

Reaction equation

HRID 1357307 reaction equation
C[O:2][C:3](=[O:41])[CH:4]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][N:24]([C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[CH3:25])[CH:19]=2)[C:14]=1[Br:40])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C1COCC1>[Br:40][C:14]1[C:15]2[C:20](=[CH:19][C:18]([CH2:23][N:24]([C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[CH3:25])=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:41])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 691377602-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester

Product 1

HCID 101214512-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acidYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(1-bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (445 mg, 0.68 mmol), prepared in the previous step, and 0.5 mL of 10% aqueous NaOH in THF was stirred at room temperature for 2.5 h. Aqueous 10% HCl was added until acidic and the reaction extracted three times with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent removed under reduced pressure to give the title compound (419 mg, 95%), MS m/z: 600 [M+H]+.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a950d150768c4350ab1ed9742ab8d388
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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