Methanol → HCID 15981117, compound

HRID 561854Notes

Reaction equation

HRID 561854 reaction equation
[CH:1]1([N:4]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=2[Cl:47])[C:5](=[O:38])[CH:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]3[C:34]([Cl:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=3[Cl:37])=[CH:21][CH:20]=2)[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[CH2:3][CH2:2]1.CO.[OH-].[Na+]>C1COCC1>[CH:1]1([N:4]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=2[Cl:47])[C:5](=[O:38])[CH:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]3[C:34]([Cl:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=3[Cl:37])=[CH:21][CH:20]=2)[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15981151HCID 15981151, compound

Product 1

HCID 15981117HCID 15981117, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[(3-[cyclopropyl(2,3-dichlorobenzyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)amino]hexanoate (Example 20, 1 eq.) was dissolved in a 2:1 (v/v) THF:MeOH solution (0.01 M). To this was then added sodium hydroxide (1.0 M aqueous solution, 3 eq.) and the resulting solution was stirred at RT for 18 h. The volatiles were then removed in vacuo. Following careful acidification of the resulting residue to a pH of ˜4 with 10% aq. HCl, the mixture was saturated with sodium chloride and extracted with EtOAc. The combined organic extracts were concentrated in vacuo. The resulting solid residue was then azeotroped with toluene to give the title compound as a white solid. MS (ESI+): 709.1.

Workup

  1. customThe volatiles were then removed in vacuo
  2. extractionextracted with EtOAc
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. customThe resulting solid residue was then azeotroped with toluene

Sources & evidence

ORD record
ord-33e6f4e3e73e4fc1ae8d37f2f16d03e0
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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