Chloroform → 4-{[1-Methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl

HRID 1519664Notes

Reaction equation

HRID 1519664 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.Cl.[CH3:21][NH:22][C:23](=[O:31])[C@H:24]([C:27](=[O:30])[O:28][CH3:29])[NH:25][CH3:26].C(N(CC)CC)C>O>[CH3:29][O:28][C:27](=[O:30])[CH:24]([N:25]([CH3:26])[C:11]([C:10]1[CH:14]=[CH:15][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=1)=[O:12])[C:23]([NH:22][CH3:21])=[O:31]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride2×

Product 1

HCID 712682154-{[1-Methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenylYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Phenylbenzoyl chloride (2.23 g) was added little by little to a chloroform (20 mL) solution of N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 2.02 g) and triethylamine (2.18 g) under ice cooling, and the mixture was stirred for 30 minutes at the same temperature and for 1 hour, with the temperature raised to room temperature. Water was added to the reaction mixture, and the system was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the desiccant was filtered out, whereafter the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=98/2→90/10) to obtain 4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (yellow solid) (3.0 g, 86%).

Workup

  1. extractionthe system was extracted with chloroform
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out, whereafter the solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=98/2→90/10)

Sources & evidence

ORD record
ord-5b99a596b05a47318e9190f141fe1b4d
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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