Hydrochloric Acid → HCID 131720270, compound

HRID 2293314Notes

Reaction equation

HRID 2293314 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:12](O)=O)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[N+:25]([C:28]1[CH:41]=[CH:40][C:31]([CH2:32][N:33]2[C:37](=[O:38])C=[CH:35][C:34]2=[O:39])=[CH:30][CH:29]=1)([O-:27])=[O:26].[ClH:42].C[N:44](C=O)C>>[ClH:42].[CH2:1]([O:8][CH2:9][CH:10]1[CH:12]2[CH:35]([C:34](=[O:39])[N:33]([CH2:32][C:31]3[CH:40]=[CH:41][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=3)[C:37]2=[O:38])[CH:21]([C:20]2[CH:23]=[CH:24][C:17]([C:15](=[NH:44])[NH2:16])=[CH:18][CH:19]=2)[NH:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 660424-CyanobenzaldehydeHCID 78457O-benzyl-L-serineHCID 10489717HCID 10489717, compound

Product 1

HCID 131720270HCID 131720270, compound

Procedure

592 mg (3 mmol) of O-benzylserine, 393 mg (3 mmol) of 4-cyano-benzaldehyde and 697 mg (3 mmol) of N-(4-nitro-benzyl)-maleimide in 25 ml of DMF were heated at 110° C. for 5 hours. After cooling the solvent was removed in a vacuum. The crude product was filtered over silica gel with hexane/ethyl acetate and the solvent was removed. Thereafter, the residue was dissolved in a methanol/chloroform (1:5) mixture and dry hydrogen chloride was introduced while cooling with ice. After standing at 4° C. for 14 hours the solution was treated with ether and the colourless precipitate was filtered off and thereafter boiled at reflux for 3 hours with a methanol solution saturated with ammonia. The solvent was removed in a vacuum. The thus-obtained crude product was treated with 3 ml of 1N hydrochloric acid and again evaporated. The yellowish residue was separated over a RP-18 chromatography column with a water/methanol gradient. 67 mg of (1RS,3RS,3aSR,6aRS)-4-[3-(benzyloxy-methyl)-5-(4-nitro-benzyl)-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl]-benzimidamide hydrochloride were isolated as a yellowish powder. ISP-MS: 514 ([M+H]+, 100).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed in a vacuum
  3. filtrationThe crude product was filtered over silica gel with hexane/ethyl acetate
  4. customthe solvent was removed
  5. dissolutionThereafter, the residue was dissolved in a methanol/chloroform (1:5) mixture and dry hydrogen chloride
  6. additionwas introduced
  7. temperaturewhile cooling with ice
  8. additionthe solution was treated with ether
  9. filtrationthe colourless precipitate was filtered off
  10. temperatureat reflux for 3 hours with a methanol solution saturated with ammonia
  11. customThe solvent was removed in a vacuum
  12. customThe thus-obtained crude product
  13. customagain evaporated
  14. customThe yellowish residue was separated over a RP-18 chromatography column with a water/methanol gradient

Sources & evidence

ORD record
ord-95c309f1373c4b07b7488fc952cc503e
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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