57227-09-5

Basic information

• Product Name: N-Benzoyl-DL-tyrosil-N',N'-dipropylamide
• Synonyms: N-BENZOYL-DL-TYROSIL-DI-N-PROPYLAMIDE;N-BENOYL-DL-TYROSIL-DI-N-PROPYLAMIDE;N-Benzoyl-DL-tyrosil-N',N'-dipropylamide;(±)-α-(BenzoylaMino)-4-hydroxy-N,N-dipropylbenzenepropanaMide;CR 1936;N-Benzoyl-DL-tyrosyl-N',N'-dipropylaMide;TiropraMide IMpurity C;Benzoyl-dl-tyrosil-di-n-propylaMide
• CAS NO: 57227-09-5
• Molecular Formula: C₂₂H₂₈N₂O₃
• Molecular Weight: 368.47
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 57227-09-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 619.102 ºC at 760 mmHg
• Flash Point: 328.221 ºC
• Appearance: /
• Density: 1.131 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.87±0.15(Predicted)
• CAS DataBase Reference: N-Benzoyl-DL-tyrosil-N',N'-dipropylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-DL-tyrosil-N',N'-dipropylamide(57227-09-5)
• EPA Substance Registry System: N-Benzoyl-DL-tyrosil-N',N'-dipropylamide(57227-09-5)

Safety Data

• Hazardous Substances Data: 57227-09-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

N-Benzoyl-DL-tyrosyl-N',N'-dipropylamide is a metabolite of the antispasmodic agent Tiropramide (T446900). Tiropramide impurity C.

Synthetic route

O.N-Dibenzoyl-DL-tyrosyl-di-n-propylamid (57227-08-4) → N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5)

Conditions	Yield
With sodium hydroxide

N-benzoyl-O-benzoyl-L-tyrosine (14325-35-0) → N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Et3N, ClCO2Et, (ii) /BRN= 505974/ 2: sodium hydroxide View Scheme

L-tyrosine (60-18-4) → N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide 2: (i) Et3N, ClCO2Et, (ii) /BRN= 505974/ 3: sodium hydroxide View Scheme

di-n-propylaminoethyl chloride (36716-60-6) + N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) → N-{2-[4-(2-Dipropylamino-ethoxy)-phenyl]-1-dipropylcarbamoyl-ethyl}-benzamide

Conditions	Yield
With sodium methylate

diethyl-(4-chloro-butyl)-amine (57227-21-1) + N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) → N-{2-[4-(4-Diethylamino-butoxy)-phenyl]-1-dipropylcarbamoyl-ethyl}-benzamide

Conditions	Yield
With sodium methylate

diethyl-(3-chloro-2-methyl-butyl)-amine (19966-44-0) + N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) → N-{2-[4-(3-Diethylamino-1,2-dimethyl-propoxy)-phenyl]-1-dipropylcarbamoyl-ethyl}-benzamide

Conditions	Yield
With sodium methylate

N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) + 2-(dimethylamino)ethyl chloride (107-99-3) → N-{2-[4-(2-Dimethylamino-ethoxy)-phenyl]-1-dipropylcarbamoyl-ethyl}-benzamide

Conditions	Yield
With sodium methylate

N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) + 2-(diethylamino)ethyl chloride (100-35-6) → Alfospas (55837-29-1)

Conditions	Yield
With sodium methylate

N-benzoyl-DL-tyrosil-di-n-propylamide (57227-09-5) + (2-chloroethyl)-diisopropylamine (96-79-7) → N-{2-[4-(2-Diisopropylamino-ethoxy)-phenyl]-1-dipropylcarbamoyl-ethyl}-benzamide

Conditions	Yield
With sodium methylate

Upstream product

• 60-18-4 L-tyrosine 
• 14325-35-0 N-benzoyl-O-benzoyl-L-tyrosine 
• 57227-08-4 O_.N-Dibenzoyl-DL-tyrosyl-di-n-propylamid 

Downstream Products

• 55837-29-1 Alfospas 

Relevant articles and documents

O-Tertiary amino-alkyl-N-benzoyl tyrosil amides

Tyrosine derivatives of the formula: STR1 wherein: R1 is a linear or branched-chain alkyl group having 1-6 carbon atoms, terminating by a tertiary amino group; R 2 is an unsubstituted, monosubstituted or di-substituted phenyl or benzyloxy group, the substituent being --Cl, --Br, --NO2, --OCH3, --CH3 or --CF3 ; R3 is a primary, secondary or tertiary amino group or an aryl-alkylamino group having 7-9 carbon atoms; and salts of said tyrosine derivatives with pharmaceutically acceptable acids.