Lithium hydroxide, monohydrate → HCID 67080211, compound

HRID 510673Notes

Reaction equation

HRID 510673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14]([C:16]1[CH:37]=[CH:36][C:19]([O:20][C:21]3[CH:30]=[C:29]4[C:24]([CH:25]([C:31]([O-:33])=[O:32])[CH2:26][CH2:27][O:28]4)=[CH:23][C:22]=3[C:34]#[N:35])=[CH:18][CH:17]=1)=[O:15])[CH2:7][CH2:6]2.O[Li].O.O1CCOCC1.Cl>C1COCC1>[C:34]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:21]=1[O:20][C:19]1[CH:18]=[CH:17][C:16]([C:14](=[O:15])[NH:13][CH:8]3[CH2:7][CH2:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:9]3)=[CH:37][CH:36]=1)[O:28][CH2:27][CH2:26][CH:25]2[C:31]([OH:33])=[O:32])#[N:35]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 86653236HCID 86653236, compound

Product 1

HCID 67080211HCID 67080211, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(4-((6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate (29.5 mg, 0.0576 mmol) was dissolved in THF (3 ml) and 1M solution of LiOH—H2O (115 μL, 0.115 mmol) was added. The mixture was stirred for 17 hours at ambient temperature. The mixture was quenched with 4M HCl dioxane (43.2 μL, 0.173 mmol). The crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 28.9 mg of the title compound as a thin film (100%). MS (apci) m/z=499.1 (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-c2b1b326207e455e9dc75dd98ed95890
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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