Lithium Hydroxide → HCID 68182738, compound

HRID 524436Notes

Reaction equation

HRID 524436 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:14]([NH:16][C:17]3[N:22]=[C:21]([CH2:23][C:24]([O:26]CC)=[O:25])[CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CCO>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:29][CH:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[C:14]([NH:16][C:17]3[N:22]=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68182436HCID 68182436, compound

Product 1

HCID 68182738HCID 68182738, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[6-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]-2-pyridyl]acetate (Example A9; 0.4 g, 0.796 mmol) was taken in THF(12 mL) and EtOH (4 mL), to it was added aqueous solution of LiOH (0.033 g, 0.796 mmol in 4 mL water) and stirred for 1 h at room temperature. Completion of reaction was confirmed by TLC. Organic solvent was removed under reduced pressure. The obtained residue was diluted with water (50 mL) and washed with ethyl acetate (2×20 mL). The aqueous layer was acidified with 1N HCl to pH 1-2 and extracted with Ethyl acetate (3×50 mL). The combined organic layer was washed with brine (50 mL) dried over anhydrous sodium sulphate and the solvent was removed under vacuum to get the pure product (0.320 g).

Workup

  1. customCompletion of reaction
  2. customOrganic solvent was removed under reduced pressure
  3. additionThe obtained residue was diluted with water (50 mL)
  4. washwashed with ethyl acetate (2×20 mL)
  5. extractionextracted with Ethyl acetate (3×50 mL)
  6. washThe combined organic layer was washed with brine (50 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-b4218933d85545c7a00fe4f0f0c4e95d
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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