Methyl chloroglyoxylate → HCID 58504269, compound

HRID 2407786Notes

Reaction equation

HRID 2407786 reaction equation
[CH3:1][O:2][CH:3]([O:34][CH3:35])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:33])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[S:26][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:24][CH:23]=2)[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C.Cl[C:46](=[O:51])[C:47]([O:49][CH3:50])=[O:48]>ClCCl.C(OCC)(=O)C>[CH3:35][O:34][CH:3]([O:2][CH3:1])[CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:33])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[S:26][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:24][CH:23]=2)[CH2:17][CH2:16]1)[C:46](=[O:51])[C:47]([O:49][CH3:50])=[O:48]

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 58504215HCID 58504215, compound

Product 1

HCID 58504269HCID 58504269, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 323 (555 mg) in dichloromethane (7.0 mL) at 0° C. was added diisopropylethylamine (0.59 mL) followed by methyl 2-chloro-2-oxoacetate (0.16 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: 80% ethyl acetate/hexane with 3% (9:1 methanol/concentrated ammonium hydroxide)) to furnish the title compound (392 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: 80% ethyl acetate/hexane with 3% (9:1 methanol/concentrated ammonium hydroxide))

Sources & evidence

ORD record
ord-532bfe765c4c4de1a5f12a8759c4fa1c
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…