Methyl chloroglyoxylate → HCID 58503982, compound

HRID 2407779Notes

Reaction equation

HRID 2407779 reaction equation
[O:1]=[C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.Cl[C:41](=[O:46])[C:42]([O:44][CH3:45])=[O:43]>ClCCl.C(OCC)(=O)C>[CH3:45][O:44][C:42](=[O:43])[C:41]([N:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:2](=[O:1])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:7][CH2:6]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:46]

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 58504041HCID 58504041, compound

Product 1

HCID 58503982HCID 58503982, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 303 (350 mg) in dichloromethane (3.0 mL) at 0° C. was added diisopropylethylamine (0.746 mL) followed by methyl 2-chloro-2-oxoacetate (262 mg). The reaction was allowed to warm to room temperature and then stirred for 2 hours. The solution was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 10% ethyl acetate/hexane) to furnish the title compound (374 mg) with the following physical properties.

Workup

  1. washwashed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude material, which
  5. customwas purified by flash column chromatography (eluant: 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ff70ac160d284c3daf7c63bd2fe44596
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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