Lithium hydroxide, monohydrate → HCID 67080304, compound

HRID 1048075Notes

Reaction equation

HRID 1048075 reaction equation
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:32]=[CH:31][C:13]([O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH:19]([C:25]([O:27]C)=[O:26])[CH2:20][CH2:21][O:22]4)=[CH:17][C:16]=3[C:29]#[N:30])=[CH:12][CH:11]=2)=[O:9])[CH:2]=1.O[Li].O.O1CCOCC1.Cl>C1COCC1>[C:1]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:32]=[CH:31][C:13]([O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH:19]([C:25]([OH:27])=[O:26])[CH2:20][CH2:21][O:22]4)=[CH:17][C:16]=3[C:29]#[N:30])=[CH:12][CH:11]=2)=[O:9])[CH:2]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 67080504HCID 67080504, compound

Product 1

HCID 67080304HCID 67080304, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 7-(4-(biphenyl-3-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (55.6 mg, 0.1102 mmol) in THF (2 ml) was added 1M solution of LiOH—H2O (220.4 μl, 0.2204 mmol). The mixture was stirred for 1 hour at ambient temperature. The mixture was quenched with 4M HCl dioxane (82.65 μl, 0.331 mmol). The crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 40.4 mg of the title compound as a thin film (75%). MS (apci) m/z=491.1 (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-72cb460d352d4755991c6169f731c780
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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