Hydrochloric Acid → Z-PyroGlu-Pro-Arg(NO2)

HRID 1197073Notes

Reaction equation

HRID 1197073 reaction equation
Cl.[NH:2]1[CH2:23][CH2:22][CH2:21][C@H:3]1[C:4]([NH:6][C@H:7]([C:18]([OH:20])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5].[N:24]1([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30](O)=[O:31]>CN(C=O)C.CC(O)=O>[N:24]1([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30]([N:2]1[CH2:23][CH2:22][CH2:21][C@H:3]1[C:4]([NH:6][C@H:7]([C:18]([OH:20])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 178512175H-Pro-Arg(NO2)

Product 1

HCID 178512171Z-PyroGlu-Pro-Arg(NO2)Yield 53.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

After 2.25 g (5.0 mmols) of HCl.H-Pro-Arg(NO2)-CHA was dissolved in 10 ml (15.0 mmols) of 1.5N NEM/DMF, 1.93 g (5.0 mmols) of Z-PyroGlu-SDP was added to the solution at 0° to 5° C. The resulting mixture was reacted at room temperature for 18 hours. After completion of the reaction, the reaction solution was diluted with 300 ml of AcOH followed by washing 4 times with 100 ml of cold 5% hydrochloric acid and twice with 100 ml of saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate and decoloring with activated charcoal, the AcOEt phase was distilled under reduced pressure. The residue was recrystallized from MeOH/AcOEt/ether to give 1.86 g (53.4%) of Z-PyroGlu-Pro-Arg(NO2)-CHA.

Workup

  1. additionwas added to the solution at 0° to 5° C
  2. customThe resulting mixture was reacted at room temperature for 18 hours
  3. customAfter completion of the reaction
  4. washby washing 4 times with 100 ml of cold 5% hydrochloric acid
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe AcOEt phase was distilled under reduced pressure
  7. customThe residue was recrystallized from MeOH/AcOEt/ether

Sources & evidence

ORD record
ord-49d03015b9294ce78b2351b73a5a2dbb
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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