Sodium Hydroxide → HCID 70977696, compound

HRID 2402406Notes

Reaction equation

HRID 2402406 reaction equation
[OH:1][C:2]1([C:15]2[S:16][C:17]([C:20]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([NH:27][C:28]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][N:29]=4)[N:21]=3)=[CH:18][N:19]=2)[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O-:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CO>[OH:1][C:2]1([C:15]2[S:16][C:17]([C:20]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([NH:27][C:28]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][N:29]=4)[N:21]=3)=[CH:18][N:19]=2)[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86680809HCID 86680809, compound

Product 1

HCID 70977696HCID 70977696, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (R or S)-5-hydroxy-5-(5-(6-((4-methoxypyridin-2-yl)amino)-4-methylpyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate (fast or slow enantiomer from step 2, 101 mg, 0.2 mmol) in MeOH (6 mL) was added a solution of sodium hydroxide (2 mL, 0.3 M, 0.6 mmol) and the mixture was heated to reflux for 1 hour. Methanol was removed under reduced pressure and the residue was diluted with 10 mL of water. The pH was adjusted to 6 with 1 M HCl, during which time a precipitate developed. The white precipitate was collected by filtration and washed with water and dried to afford (R or S)-5-hydroxy-5-(5-(6-((4-methoxypyridin-2-yl)amino)-4-methylpyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customMethanol was removed under reduced pressure
  4. additionthe residue was diluted with 10 mL of water
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-43e309bc4fcf44648964197972ec4f32
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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