Stannous chloride dihydrate → HCID 178476715, compound

HRID 1952999Notes

Reaction equation

HRID 1952999 reaction equation
[NH2:1][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:42])[C@@H:15]([CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:41])=[N:37][N+]([O-])=O)[NH:16][C:17](=[O:31])[CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:7]=1)=[O:3].[OH2:43].O.[Sn](Cl)Cl>C(O)=O>[NH2:1][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:42])[C@@H:15]([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:37])[NH2:41])[NH:16][C:17](=[O:31])[CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][CH:7]=1)=[O:3].[C:17]([O-:31])(=[O:43])[CH3:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 136333685HCID 136333685, compound

Product 1

HCID 178476715HCID 178476715, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

0.7 g (1.216 mMol) of (R)-N-[[4-(Aminocarbonyloxymethyl)-phenyl]methyl]-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)ornithinamide were dissolved in 50 ml of 60% aqueous formic acid, mixed with 2.7 g (11.97 mMol) of tin(II)-chloride-dihydrate and heated to +50° C. for 10 minutes. 20 ml of formic acid were added and the mixture was maintained at +50° C. for a further 72 hours. It was evaporated down in vacuo. the residue was taken up in methanol and filtered to remove the insoluble matter. It was evaporated down once more, the residue remaining was taken up in saturated aqueous soda solution and suction filtered. The crystals were treated once more with methanol, then filtered, the filtrate was evaporated down and carefully freed from any accompanying matter by column chromatography on silica gel (Baker; 0.03-0.06 mm) using ethyl acetate/methanol/glacial acetic acid=70/30/1 (v/v/v) as eluant. 40 mg (5.6% of theory) of a colourless, glassy-amorphous substance were obtained.

Workup

  1. temperatureheated to +50° C. for 10 minutes
  2. temperaturethe mixture was maintained at +50° C. for a further 72 hours
  3. customIt was evaporated down in vacuo
  4. filtrationfiltered
  5. customto remove the insoluble matter
  6. customIt was evaporated down once more
  7. filtrationfiltered
  8. additionThe crystals were treated once more with methanol
  9. filtrationfiltered
  10. customthe filtrate was evaporated down
  11. custom40 mg (5.6% of theory) of a colourless, glassy-amorphous substance were obtained

Sources & evidence

ORD record
ord-4a134da3cd5d43d58c93c8ecea406e37
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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