L-Alaninol → HCID 49801027, compound

HRID 1807518Notes

Reaction equation

HRID 1807518 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[CH:8][O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].C(C1C(COC2C=CC(C(O)=O)=CN=2)=C(C)ON=1)CCC.[NH2:42][C@@H:43]([CH3:46])[CH2:44][OH:45]>>[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:42][C@@H:43]([CH3:46])[CH2:44][OH:45])=[O:18])=[CH:14][N:13]=2)=[CH:8][O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 80307L-AlaninolHCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acidHCID 66643575HCID 66643575, compound

Product 1

HCID 49801027HCID 49801027, compoundYield 79%

Procedure

As described for example 19b, 6-(3-butyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.72 mmol) was converted, instead of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid, using (S)-(+)-2-amino-1-propanol instead of rac-2,2,2-trifluoro-1-(methyl)ethylamine, to the title compound (190 mg, 79%) which was obtained as a white solid after purification by chromatography (silica, heptane:ethyl acetate 7:3 to 0:1). MS: m/e=332.1 [M−H]−.

Sources & evidence

ORD record
ord-7e4adcd633df434ab6e683364ef589f0
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

Loading…