Methyl chloroglyoxylate → HCID 58504089, compound

HRID 2407789Notes

Reaction equation

HRID 2407789 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:38])[CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:49](=[O:54])[C:50]([O:52][CH3:53])=[O:51]>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:38])[CH2:23][CH2:24][CH:25]1[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:29][CH2:30]1)[C:49](=[O:54])[C:50]([O:52][CH3:53])=[O:51])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 58504055HCID 58504055, compound

Product 1

HCID 58504089HCID 58504089, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 326 (620 mg) in dichloromethane (10.0 mL) at 0° C. was added diisopropylethylamine (0.82 mL) followed by methyl 2-chloro-2-oxoacetate (0.22 mL). 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 sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 50% ethyl acetate/hexane) to furnish the title compound (722 mg) with the following physical properties.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-56e9f92044b84a92b94e06fae6f96319
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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