Diisopropylethylamine → HCID 71268190, compound

HRID 1519691Notes

Reaction equation

HRID 1519691 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:25]([O:27][C:28](=[O:37])[C@@:29]([CH3:36])([C:32]([NH:34][CH3:35])=[O:33])[NH:30][CH3:31])[CH3:26].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:25]([O:27][C:28](=[O:37])[C:29]([N:30]([CH3:31])[C:20]([C:19]1[CH:23]=[CH:24][C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:17][CH:18]=1)=[O:21])([CH3:36])[C:32]([NH:34][CH3:35])=[O:33])[CH3:26]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 841514-Phenylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 86679250HCID 86679250, compound2×

Product 1

HCID 71268190HCID 71268190, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DIPEA (1.0 mL) and 4-phenylbenzoyl chloride (0.50 g) were added in this order to a chloroform (10 mL) solution of O-ethyl-N,N2,2-trimethyl-3-oxoserinamide (Intermediate 9-1, 0.69 g), and the mixture was stirred for 5 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, whereafter the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=60/40→25/75) to obtain 4-{[1-ethoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (colorless oil) (0.79 g, 66%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, whereafter the desiccant
  3. filtrationwas filtered out
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=60/40→25/75)

Sources & evidence

ORD record
ord-b491a0ed7a2e454bbb044a8476d55445
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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