Lithium hydroxide, monohydrate → HCID 67107892, compound

HRID 2177786Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]C)=[O:18])=[C:15]([O:21][CH2:22][CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])[C:14]([C:33]3[CH:37]=[CH:36][O:35][CH:34]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O.O1CCOCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:21][CH2:22][CH2:23][N:24]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH3:25])[C:14]([C:33]3[CH:37]=[CH:36][O:35][CH:34]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoate (Intermediate 125, 0.054 g) was added to a solution of lithium hydroxide monohydrate (0.034 g) in water (0.3 ml) and dioxane (1 ml) and the mixture was stirred and heated at 130° C. for 30 minutes. The reaction mixture was cooled to room temperature, and partitioned between water and ethyl acetate. The aqueous layer was acidified with formic acid and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoic acid (0.043 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between water and ethyl acetate
extractionextracted with ethyl acetate
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-5d67f42e610f4c5595df2a8d10c6fd16
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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