Diisopropylethylamine → HCID 136333688, compound

HRID 1953001Notes

Reaction equation

HRID 1953001 reaction equation
[NH2:1][C:2](=[N:36][N+:37]([O-:39])=[O:38])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=1)=[O:25])[NH:8][C:9](=[O:23])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+]([NH:43][C:44]([NH:46][C:47](N)=[O:48])=[O:45])([O-])=O.C(N(C(C)C)CC)(C)C>CO>[NH2:43][C:44]([NH:46][C:47]([NH:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][NH:26][C:24](=[O:25])[C@@H:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2]([NH2:1])=[N:36][N+:37]([O-:39])=[O:38])[NH:8][C:9](=[O:23])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:33][CH:32]=1)=[O:48])=[O:45]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 4164621-Nitrobiuret2×HCID 136333687HCID 136333687, compound

Product 1

HCID 136333688HCID 136333688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.53 g (0.997 mMol) of (R)-N5 -[amino(nitroimino)-methyl]-N-[[4-(aminomethyl)phenyl]methyl]-N2 -(diphenylacetyl)-ornithinamide, 0.16 g (1.08 mMol) of nitrobiuret, 50 ml of methanol and 0.2 ml of diisopropylethylamine was refluxed for 5 hours with stirring. The same amount of nitrobiuret and diisopropylethylamine was added again and the mixture was refluxed for a further 3 hours. The crystals obtained after leaving the mixture to stand for 14 hours at ambient temperature were suction filtered, washed thoroughly with methanol and diethylether and dried in vacuo. 0.51 g (83% of theory) of colourless crystals were obtained, Mp. 214-218° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturethe mixture was refluxed for a further 3 hours
  3. customThe crystals obtained
  4. customafter leaving the mixture
  5. filtrationfiltered
  6. washwashed thoroughly with methanol and diethylether
  7. customdried in vacuo
  8. custom0.51 g (83% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-cbecd5f1c5814b36931cd0492afb43eb
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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