Lithium hydroxide, monohydrate → HCID 67080362, compound

HRID 1021466Notes

Reaction equation

HRID 1021466 reaction equation
CC1C=CC([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[CH:39]=[CH:38][C:20]([O:21][C:22]4[CH:31]=[C:30]5[C:25]([CH:26]([C:32]([O:34]C)=[O:33])[CH2:27][CH2:28][O:29]5)=[CH:24][C:23]=4[C:36]#[N:37])=[CH:19][CH:18]=3)=[O:16])=[CH:10][CH:9]=2)=CC=1.O[Li].O.O1[CH2:48][CH2:47]OCC1.Cl>C1COCC1>[C:36]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:22]=1[O:21][C:20]1[CH:38]=[CH:39][C:17]([C:15](=[O:16])[NH:14][C:11]3[CH:10]=[C:9]([C:8]4[CH:13]=[CH:12][C:47]([CH3:48])=[CH:10][CH:9]=4)[CH:8]=[CH:13][CH:12]=3)=[CH:18][CH:19]=1)[O:29][CH2:28][CH2:27][CH:26]2[C:32]([OH:34])=[O:33])#[N:37]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 67080537HCID 67080537, compound

Product 1

HCID 67080362HCID 67080362, compoundYield 187.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 7-(4-(4′-methylbiphenyl-4-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (33 mg, 0.063 mmol), 1M solution of LiOH—H2O (127.3 μl, 0.127 mmol), and THF (1.5 ml) was stirred for 17 hours at ambient temperature. The mixture was quenched with 4M HCl dioxane (47.73 μL, 0.190 mmol). The crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 29.8 mg of the title compound as a white solid (93%). MS (apci) m/z=505.1 (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-3b93540931c34ad9b4468757e722b4f7
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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