Diisopropylethylamine → N,N'-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid

https://huagongshe.com/reaction/1949615

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Paromomycin Sulfate	HCID 441375	—
Reactant	Phenylmethyl N-((((phenylmethoxy)carbonyl)amino)-1H-pyrazol-1-ylmethylene)carbamate	HCID 3563804	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N,N'-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid	HCID 66728201	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a stirring solution of 2(S)-hydroxy-4-amino-butyric acid (1, 0.059 g, 0.50 mmol) in DMF (2 ml) was added N,N′-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (0.26 g, 0.70 mmol) followed by DIPEA (0.87 mL, 4.99 mmol) and the reaction was heated to 80° C. and stirred overnight. The crude mixture was purified on a 2-inch reverse-phase HPLC column to yield N,N′-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid (2): MS: m/z (M+H)+ calc. 430.15, obs. 430.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08399419B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-7511fdd707fb47da82c9e26ac6e0aac7
Source note	uspto-grants-2013_03