Hydrochloric Acid → HCID 10211791, compound

HRID 1357289Notes

Reaction equation

HRID 1357289 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:48])[CH:6]([O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:25][N:26]([CH3:46])[C:27]([C:29]3[O:30][C:31]4[CH:45]=[CH:44][CH:43]=[CH:42][C:32]=4[C:33]=3[CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:28])[CH:21]=2)[C:16]=1[Br:47])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>CO>[Br:47][C:16]1[C:17]2[C:22](=[CH:21][C:20]([CH2:25][N:26]([CH3:46])[C:27]([C:29]3[O:30][C:31]4[CH:45]=[CH:44][CH:43]=[CH:42][C:32]=4[C:33]=3[CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:28])=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[O:14][CH:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:48])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 12083583HCID 12083583, compound

Product 1

HCID 10211791HCID 10211791, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 N NaOH (5 mL, 5 mmol) and 2-(1-bromo-6-{[methyl-(3-phenethyl-benzofuran-2-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (1.68 g, 2.49 mmol), prepared in the previous step, in 110 mL of methanol plus 5 mL of water was stirred under nitrogen at room temperature overnight. 1 N HCl (50 mL, 50 mmol) was added and the reaction was concentrated under reduced pressure to remove the methanol. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (1.20 g, 73%) as a white solid, mp 87-90° C.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customto remove the methanol
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-210d8bfed5a341659a861de952397757
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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