Benzaldehyde → HCID 178476711, compound

HRID 2293298Notes

Reaction equation

HRID 2293298 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:21]([N:28]1[C:32](=[O:33])[CH:31]=[CH:30][C:29]1=[O:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(=O)C.CO>[C:10]([OH:12])(=[O:11])[CH3:2].[CH2:21]([N:28]1[C:32](=[O:33])[CH:31]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:1][C:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[NH:9])([C:10]([OH:12])=[O:11])[CH:30]2[C:29]1=[O:34])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 74204BenzylmaleimideHCID 178418600HCID 178418600, compound

Product 1

HCID 178476711HCID 178476711, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

871 mg (5 mmol) of arginine, 530 mg (5 mmol) of benzaldehyde, 1.122 g (6 mmol) of N-benzylmaleimide and 25 drops of acetic acid were heated under reflux in 25 ml of methanol for 60 hours. After cooling the colourless precipitate was filtered off under suction and washed with ether. 1.367 g of (1RS,3SR,3aRS,6aSR)-5-benzyl-1-(3-guanidino-propyl)-4,6-dioxo-octahydro-3-phenyl-pyrrolo[3,4-c]-pyrrole-1-carboxylic acid acetate (54%) were isolated as a colourless powder. M.p.: from 195° C. decomposition. ISP-MS: 450.4 ([M+H]+, 100).

Workup

  1. temperatureAfter cooling the colourless precipitate
  2. filtrationwas filtered off under suction
  3. washwashed with ether

Sources & evidence

ORD record
ord-5053d3e8cc5140d59e8dc3493b1a4ea7
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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