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

HRID 1939811Notes

Reaction equation

HRID 1939811 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-0a02067269114513adc13f33e2d13580
Source dataset
uspto-grants-1997_12
Patent number
US05696270

Reaction notes

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