L-Alaninol → HCID 49801312, compound

HRID 1807532Notes

Reaction equation

HRID 1807532 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[CH3:25][C@H:26]([NH2:29])[CH2:27][OH:28]>>[OH:28][CH2:27][C@@H:26]([NH:29][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1)[CH3:25]

Participants

3

Reactant 2

HCID 80307L-AlaninolHCID 66643519HCID 66643519, compound

Product 1

HCID 49801312HCID 49801312, compoundYield 27%

Conditions

Temperature
50 °C

Procedure

A mixture of 6-[5-methyl-3-(tetrahydro-pyran-4-yl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.3 mol), S-(+)-2-amino-1-propanol (28.8 μL, 0.36 mmol) and TBD (12.8 mg, 0.09 mmol) was heated at 50° C. for 18 h under argon. The reaction mixture was concentrated onto silica then purified by chromatography (silica, 0 to 15% methanol in ethyl acetate) to give the title compound (30 mg, 27%) as a white solid. MS: m/e=374.4 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated onto silica
  2. customthen purified by chromatography (silica, 0 to 15% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-a421ec89d9f6408fbf3acce37a47d6bf
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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