Hydrochloric Acid → HCID 72188428, compound

HRID 881736Notes

Reaction equation

HRID 881736 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]45[CH2:31][CH2:30][C:27]([CH2:32][C:33]([O-:35])=[O:34])([CH2:28][CH2:29]4)[O:26][CH2:25]5)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2].[Li+].[OH-].Cl>C1COCC1.O>[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]45[CH2:29][CH2:28][C:27]([CH2:32][C:33]([OH:35])=[O:34])([CH2:30][CH2:31]4)[O:26][CH2:25]5)=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86700841HCID 86700841, compound

Product 1

HCID 72188428HCID 72188428, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(4′-(2-ethyl-4-methyloxazole-5-carboxamido)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (159 mg, 0.325 mmol) in THF (3 ml) at room temperature was added 1N LiOH (0.391 ml, 0.391 mmol). The mixture was stirred at room temperature overnight. The mixture was quenched with 1N HCl (0.391 ml, 0.391 mmol) and diluted with H2O. The THF was removed in vacuo to afford off-white slurry. The slurry was stirred for 15 min then filtered. The filter cake was washed with H2O, heptane, and dried to afford the title compound as off-white sold (135 mg, 87% yield).

Workup

  1. customThe THF was removed in vacuo
  2. customto afford off-white slurry
  3. stirringThe slurry was stirred for 15 min
  4. filtrationthen filtered
  5. washThe filter cake was washed with H2O, heptane
  6. customdried

Sources & evidence

ORD record
ord-6b1904d3efc14c949180d1a4c9836bef
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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