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

HRID 1081173Notes

Reaction equation

HRID 1081173 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-07a448aeeba144e28e0f5e6a97a9ae49
Source dataset
uspto-grants-1996_12
Patent number
US05583232

Reaction notes

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