Methylamine → HCID 18739112, compound

HRID 1934688Notes

Reaction equation

HRID 1934688 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([O:15]C)=O)[CH2:11][C@H:10]([NH:17][C:18]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:19]=2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:41][NH2:42]>CO>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](=[O:15])[NH:42][CH3:41])[CH2:11][C@H:10]([NH:17][C:18]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:19]=2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[O:21])[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 18739114HCID 18739114, compound

Product 1

HCID 18739112HCID 18739112, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[(3S,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-ylamino]-N-(3,4-dimethoxylbenzyl)-5-nitrobenzamide (143 mg) and 30% methanol solution of methylamine (4 mL) was stirred for one day at ambient temperature. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over magnesium sulfate. The residue was subjected to a silica gel column chromatography eluting with ethyl acetate to give 2-[(3S,5S)-1-(tert-butoxycarbonyl)-5-(methylcarbamoyl)pyrrolidin-3-ylamino]-N-(3,4-dimethoxylbenzyl)-5-nitrobenzamide (149 mg).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-dc2c279007354149b940a4ed37f74174
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…