Lithium hydroxide, monohydrate → 7-(4-(Chroman-3-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid

HRID 1048066Notes

Reaction equation

HRID 1048066 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12]([C:14]2[CH:36]=[CH:35][C:17]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]([C:29]([O:31]C)=[O:30])[CH2:24][CH2:25][O:26]4)=[CH:21][C:20]=3[C:33]#[N:34])=[CH:16][CH:15]=2)=[O:13])[CH2:2]1.O[Li].O.O1CCOCC1.Cl>C1COCC1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][O:26]4)=[CH:21][C:20]=3[C:33]#[N:34])=[CH:35][CH:36]=2)=[O:13])[CH2:2]1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 67080409methyl 7-(4-(chroman-3-ylcarbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 670802477-(4-(Chroman-3-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-(4-(chroman-3-ylcarbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate (27.6 mg, 0.0570 mmol) was dissolved in THF (3 ml) and 1M solution of LiOH—H2O (114 μL, 0.114 mmol) was added. The mixture was stirred for 17 hours at ambient temperature. The mixture was quenched with 4M HCl dioxane (42.7 μL, 0.171 mmol). The crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 21.2 mg of the title compound as white a solid (79%). MS (apci) m/z=471.0 (M+H).

Workup

  1. customThe crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient)

Sources & evidence

ORD record
ord-e8bba7928a4744c691f28a8360daa4e0
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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