Sodium Hydroxide → HCID 49806224, compound

HRID 1627937Notes

Reaction equation

HRID 1627937 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[CH:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]([O:25]C)=[O:24].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:3]=1[CH:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49806225HCID 49806225, compound

Product 1

HCID 49806224HCID 49806224, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 2-[2-methyl-4-(phenyloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate 18 mg, 0.041 mmol) in methanol (0.5 mL) was added a solution of sodium hydroxide 10 N (50 μl, 0.500 mmol) and the mixture was heated at 65° C. for 18 h. After cooling, the organic volatiles were removed under reduced pressure and the aqueous phase was then acidified with a solution of hydrochloric acid 2N until a precipitate was formed. The solid was filtered, washed with water and dried under reduced pressure to afford 0.006 g (34%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe organic volatiles were removed under reduced pressure
  3. customwas formed
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-dc1c77d0fd744fc4bc2dd6602680a887
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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