Benzyloxycarbonylglycine → HCID 178446046, compound

HRID 2309485Notes

Reaction equation

HRID 2309485 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[C:13]([NH:23][CH2:24][C:25]([OH:27])=O)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>CN(C)C=O>[C:13]([NH:23][C@H:24]([C:25]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])=[O:27])[CH2:16][CH:17]([CH3:22])[CH3:18])([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14]

Participants

4

Reactant 2

HCID 14349BenzyloxycarbonylglycineHCID 178418600HCID 178418600, compound

Product 1

HCID 178446046HCID 178446046, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.74 g (10.00 mM) of arginine are suspended in 25 ml of dimethylformamide, the solution is added with 4,25 g (11.00 mM) of p-nitrophenyl ester of carbobenzoxy-glycine, the mixture is stirred at room temperature for one day. Dimethylformamide is evaporated, the residue is dissolved in 5 ml of methanol and added with 300 ml of ether. The resulting precipitate is filtered-off, washed with ether on the filter and dried in a vacuum desiccator to give 4.05 g (96%) of carbobenzoxy-leucyl-arginine, m.p. 126°-130° C.

Workup

  1. customDimethylformamide is evaporated
  2. dissolutionthe residue is dissolved in 5 ml of methanol
  3. additionadded with 300 ml of ether
  4. washwashed with ether on the
  5. filtrationfilter
  6. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-b961f8d849404ec6b0c594097847c4c5
Source dataset
uspto-grants-1987_09
Patent number
US04695622

Reaction notes

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