Sodium Carbonate → HCID 178452036, compound

HRID 2289050Notes

Reaction equation

HRID 2289050 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:17])[CH2:15][NH2:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18](=[O:21])([O-:20])[O-].[Na+].[Na+].[C:24](S(O)(=O)=O)([NH2:26])=[NH:25].Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33].[OH-:45].[Na+]>O.O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:17])[C:15]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=2)=[O:33])([C:18]([O:20][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:43])=[O:45])=[CH:38][CH:37]=2)=[O:21])[NH:16][C:24]([NH2:26])=[NH:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 782054-Nitrobenzyl chloroformateHCID 9877361Methanesulfonic acid, aminoimino-HCID 118068461,1-Dimethylethyl (3S)-3-[(2-aminoacetyl)amino]-1-pyrrolidinecarboxylate

Product 1

HCID 178452036HCID 178452036, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S)-1-(tert-butoxycarbonyl)-3-(aminoacetylamino)pyrrolidine (2.50 g) in water (35 ml), sodium carbonate (1.31 g) and formamidinesulfonic acid (1.53 g) were added under ice cooling and the mixture was stirred overnight at room temperature. To the reaction mixture, tetrahydrofuran (30 ml) was added. To the resulting mixture, a solution of p-nitrobenzyl chloroformate (4.43 g) in tetrahydrofuran (20 ml) and a 1N aqueous sodium hydroxide solution (21 ml) were simultaneously added dropwise, followed by stirring at the same temperature for one hour. To the reaction mixture, ethyl acetate was added. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure, whereby (3S)-1-(tert-butoxycarbonyl)-3-[di(4-nitrobenzyloxycarbonyl)guanidinoacetylamino]pyrrolidine was obtained. The product was provided for the subsequent step.

Workup

  1. stirringby stirring at the same temperature for one hour
  2. washThe resulting mixture was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f8044083f4944cbc85aec1b1d7193d34
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

Loading…