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

HRID 52729

Reaction equation

HRID 52729 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:32])[C@H:15]([CH:29](C)C)[NH:16][C:17]([O:19]C1C=CC([N+]([O-])=O)=CC=1)=O.COC(=O)[C@H](C)NC(OC1C=CC([N+]([O-])=O)=CC=1)=O>>[CH3:12][O:13][C:14](=[O:32])[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

4

Reactant 3

HCID 108207841-(2-isopropyloxazol-4-yl)-N-methylmethanamineHCID 15344176Methyl N-[(4-nitrophenoxy)carbonyl]-L-valinateHCID 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 relacing 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-636ca2154b8340fd87a2cf1b2626271e
Source dataset
uspto-grants-1997_04
Patent number
US05616720

Linked notes

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