Methanol → 3-[2-[[2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]oxybenzoic acid

HRID 524432Notes

Reaction equation

HRID 524432 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[C:14]([NH:16][C:17]3[S:18][C:19]([O:22][C:23]4[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=4)[C:26]([O:28]CC)=[O:27])=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CO.[Li+].[OH-]>C1COCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[C:14]([NH:16][C:17]3[S:18][C:19]([O:22][C:23]4[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=4)[C:26]([OH:28])=[O:27])=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86669551Ethyl 3-[2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]oxybenzoate

Product 1

HCID 565918413-[2-[[2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]oxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl3-[2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]oxybenzoate (Example A2; 16 g, 27 mmol) was taken in THF (200 mL) and Methanol (100 mL) in a 1 L single necked round bottom flask at 20-25° C. To it was added solution of LiOH (11.44 g in 200 mL water, 272 mmol) slowly under vigorous stirring for 15 minutes and further continued to stir for 16 hours. Completion of reaction was confirmed by TLC. Organic solvent was removed under reduced pressure. The obtained residue was diluted with water (200 mL) and washed with ethyl acetate (2×150 mL). The aqueous layer was acidified with 1N HCl to pH 1-2 and extracted with Ethyl acetate (3×150 mL). The combined organic layer was washed with brine (150 mL) dried over anhydrous sodium sulphate and the solvent was removed under vacuum to get the pure product.

Workup

  1. customat 20-25° C
  2. stirringto stir for 16 hours
  3. customCompletion of reaction
  4. customOrganic solvent was removed under reduced pressure
  5. additionThe obtained residue was diluted with water (200 mL)
  6. washwashed with ethyl acetate (2×150 mL)
  7. extractionextracted with Ethyl acetate (3×150 mL)
  8. washThe combined organic layer was washed with brine (150 mL)
  9. dry with materialdried over anhydrous sodium sulphate
  10. customthe solvent was removed under vacuum
  11. customto get the pure product

Sources & evidence

ORD record
ord-d70bac4f43c44f18b7be74492edf1783
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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