HCID 53810510, compound → HCID 19854806, compound

HRID 1649794Notes

Reaction equation

HRID 1649794 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:33])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([O:31]C)=[O:30])[CH:25]=[N:26][CH:27]=2)=[CH:4][C:3]=1[Cl:34]>CO.[OH-].[Na+]>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:33])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[N:26][CH:27]=2)=[CH:4][C:3]=1[Cl:34]

Participants

4

Reactant 1

HCID 53810510HCID 53810510, compound

Product 1

HCID 19854806HCID 19854806, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 5-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]propyl]-3-pyridineacetate (600 mg) in methanol (10 ml) and 2N sodium hydroxide (10 ml) was stirred at room temperature for 10 min. Dowex (50) H+ methanol washed resin was added portionwise until pH 7. The resin was filtered off, the solution concentrated in vacuo to give a brown solid which was triturated in ethanol/methanol (1:2) to give the title compound as a light brown solid (250 mg), m.p. 191°-192° t.l.c. (methanol) Rf 0.6.

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe solution concentrated in vacuo
  3. customto give a brown solid which
  4. customwas triturated in ethanol/methanol (1:2)

Sources & evidence

ORD record
ord-46ab84a9766d459585c3d81c1c445f91
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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