Serinol → HCID 49782042, compound

HRID 1923549Notes

Reaction equation

HRID 1923549 reaction equation
CO[C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][C:6]=1[CH3:22])=[O:4].[NH2:23][CH:24]([CH2:27][OH:28])[CH2:25][OH:26]>C1(C)C=CC=CC=1>[OH:26][CH2:25][CH:24]([NH:23][C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][C:6]=1[CH3:22])=[O:4])[CH2:27][OH:28]

Participants

4

Reactant 2

HCID 68294SerinolHCID 666436812-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 49782042HCID 49782042, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid methyl ester (100 mg, 0.31 mmol) in toluene (1.0 mL) was added 2-amino-1,3-propandiol (57 mg, 0.62 mmol) and TBD (13 mg, 0.09 mmol). After 15 h the reaction mixture was concentrated in vacuo then purified by chromatography (silica, 0 to 7.5% methanol in dichloromethane) to give the title compound (65 mg, 55%) as an off white oil.

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. customthen purified by chromatography (silica, 0 to 7.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4bb0e759d19c4a07b5aa3624c9c2e667
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…