1-(2-isopropyloxazol-4-yl)-N-methylmethanamine → N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-alanine Methyl Ester

HRID 2258249Notes

Reaction equation

HRID 2258249 reaction equation
[CH:1]([C:4]1[O:5][CH:6]=[C:7]([CH2:9][NH:10][CH3:11])[N:8]=1)([CH3:3])[CH3:2].[CH3:12][O:13][C:14](=[O:30])[C@H:15]([CH3:29])[NH:16][C:17]([O:19]C1C=CC([N+]([O-])=O)=CC=1)=O>>[CH3:12][O:13][C:14](=[O:30])[C@H:15]([CH3:29])[NH:16][C:17]([N:10]([CH3:11])[CH2:9][C:7]1[N:8]=[C:4]([CH:1]([CH3:2])[CH3:3])[O:5][CH:6]=1)=[O:19]

Participants

3

Reactant 2

HCID 108207841-(2-isopropyloxazol-4-yl)-N-methylmethanamineHCID 54298210N-(((4-nitrophenyl)oxy)carbonyl)-L-alanine methyl ester

Product 1

HCID 10708114N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-alanine Methyl EsterYield 66%

Procedure

Using the procedure of Example 1S, but replacing 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole with 2-isopropyl-4-(((N-methyl)amino)methyl)-oxazole and replacing N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester with N-(((4-nitrophenyl)oxy)carbonyl)-L-alanine methyl ester provided the desired compound in 66 % yield. 1H NMR (CDCl3) δ1.32 (d, 6H), 1.42 (d, 3H), 2.96 (s, 3H), 3.05 (m, 1H), 3.75 (s, 3H), 4.30 (s, 2H), 4.47 (m, 1H), 5.80 (br d, 1H), 7.46 (s, 1H). Mass spectrum: (M+H)+ 284.

Sources & evidence

ORD record
ord-e8ae65e1237f42f9a258fb2b691132fd
Source dataset
uspto-grants-1997_08
Patent number
US05659045

Reaction notes

Loading…