Tetrahydrofuran → 4-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid

HRID 14609Notes

Reaction equation

HRID 14609 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:26])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:16][CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].C1COCC1.O.[OH-].[Li+]>O>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=2)=[O:26])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 686874114-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160682704-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (41 mg) in a 1:1 mixture of THF and water (2.25 mL) was added lithium hydroxide monohydrate and the reaction mixture was stirred for 20 hours at room temperature. After such time the THF was evaporated off in vacuo and the remaining aqueous phase was neutralized by addition of a 1N HCl solution. The resulting precipitate was then isolated by filtration, washed with water, and dried in vacuo to yield the title compound as a light yellow solid. MS (m/e): 354.1 (M+H−).

Workup

  1. customAfter such time the THF was evaporated off in vacuo
  2. additionthe remaining aqueous phase was neutralized by addition of a 1N HCl solution
  3. customThe resulting precipitate was then isolated by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0ad4f84618bd4c04aced8d8e9bdda5e0
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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