Lithium hydroxide, monohydrate → HCID 67080211, compound

HRID 1021440Notes

Reaction equation

HRID 1021440 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-dedc1aa2d6b24e458ac8ff6a8589bfa7
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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