Lithium hydroxide, monohydrate → HCID 67080211, compound

HRID 1048068Notes

Reaction equation

HRID 1048068 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-0fa1f7786f954ddba30f5855ab13c4f8
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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