Water → HCID 86594824, compound

HRID 346873Notes

Reaction equation

HRID 346873 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][O:11][N:12]=[CH:13][C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].O>C1COCC1>[O:18]1[C:17]2[CH:22]=[CH:23][C:14]([CH:13]=[N:12][O:11][CH2:10][C:7]3[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)=[CH:15][C:16]=2[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86594825HCID 86594825, compound

Product 1

HCID 86594824HCID 86594824, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 200 mg (0.60 mmol) 5-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carboxylic acid methyl ester in 2.4 ml THF were added 1.2 ml 1M aqueous LiOH solution and the reaction mixture was heated to 70° C. for 5 h. Water was added, the mixture was acidified and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4 and the solvent was evaporated to give 190 mg (0.59 mmol) 5-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carbox-ylic acid; exact MW [M+H] calc'd: 320.06; MW found [M+H]: 320.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-30d929c3332644309c400ac3b39709d2
Source dataset
uspto-grants-2007_02
Patent number
US07173060B2

Reaction notes

Loading…