Sodium Hydroxide → HCID 25119358, compound

HRID 1798479Notes

Reaction equation

HRID 1798479 reaction equation
[CH:1]1([N:4]([CH2:32][C:33]2[CH:34]=[C:35]([CH:48]=[C:49]([CH2:51][CH2:52][CH2:53][O:54][CH3:55])[CH:50]=2)[O:36][CH2:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44]C)=[O:43])=[CH:40][CH:39]=2)[C:5]([C@@H:7]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[Cl:31])=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([N:4]([CH2:32][C:33]2[CH:34]=[C:35]([CH:48]=[C:49]([CH2:51][CH2:52][CH2:53][O:54][CH3:55])[CH:50]=2)[O:36][CH2:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)[C:5]([C@@H:7]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[Cl:31])=[CH:17][CH:18]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25119359HCID 25119359, compound

Product 1

HCID 25119358HCID 25119358, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-{[3-({cyclopropyl[((3R,4S)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl]amino}methyl)-5-(3-methoxypropyl)phenoxy]methyl}benzoate (1 eq.) from Example 18 in methanol (0.03) was added 1 N aqueous NaOH (2.2 eq.). The reaction was heated to reflux and stirred for 18 h. The volatiles were removed in vacuo and the resulting solid residue was triturated with ether. The resulting residue was then taken up in EtOAc and the insolubles were removed via filtration. To the filtrate was then slowly added ether to precipitate out the sodium salt of the title compound as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customThe volatiles were removed in vacuo
  4. customthe resulting solid residue was triturated with ether
  5. customthe insolubles were removed via filtration
  6. customslowly added ether to precipitate out the sodium salt of the title compound as a white solid

Sources & evidence

ORD record
ord-f37f0874023a4abd9c0eb29d47ce1a87
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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