Ethanol → HCID 71268205, compound

HRID 1519692Notes

Reaction equation

HRID 1519692 reaction equation
[OH-].[K+].C(O)C.C([O:8][C:9](=[O:32])[C:10]([N:16]([CH3:31])[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:18])([CH3:15])[C:11]([NH:13][CH3:14])=[O:12])C.S([O-])(O)(=O)=O.[K+]>O.C1COCC1>[C:9]([C:10]([N:16]([CH3:31])[C:17]([C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)=[O:18])([CH3:15])[C:11]([NH:13][CH3:14])=[O:12])([OH:32])=[O:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 71268190HCID 71268190, compound

Product 1

HCID 71268205HCID 71268205, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0.84 mol/L potassium hydroxide aqueous solution (3.0 mL) was added to an ethanol (3.0 mL)-THF (3.0 mL) solution of 4-{[1-ethoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (0.30 g) as obtained in Example 12-(1), and the mixture was stirred for 4.5 hours at room temperature. Under ice cooling, water and a 2.0 mol/L potassium hydrogen sulfate aqueous solution were added to adjust the mixture to pH 7, followed by extracting the mixture with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the desiccant was filtered out. The solvent was distilled off under reduced pressure to obtain 4-{[2-carboxy-1-(methylamino)-1-oxopropan-2-yl](methyl)carbamoyl}biphenyl (orange solid) (0.29 g, 82%).

Workup

  1. customas obtained in Example 12-(1)
  2. extractionby extracting the mixture with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered out
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fae2df811a0944cbb921891e45880b98
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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