Methyl 2-amino-1,3-thiazole-4-carboxylate → HCID 86604052, compound

HRID 2222974Notes

Reaction equation

HRID 2222974 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([C:18](F)=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]([C:26]1[N:27]=[C:28]([NH2:31])[S:29][CH:30]=1)=[O:25]>O1CCOCC1>[CH3:22][O:23][C:24]([C:26]1[N:27]=[C:28]([NH:31][C:18](=[O:19])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]#[N:17])[S:29][CH:30]=1)=[O:25]

Participants

4

Reactant 2

HCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 86604053HCID 86604053, compound

Product 1

HCID 86604052HCID 86604052, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

[(S)-2-(2-Cyano-phenyl)-1-fluorocarbonyl-ethyl]-carbamic acid tert-butyl ester (2.4 g, 8.2 mmol) and 2-amino-thiazole-4-carboxylic acid methyl ester (1.24 g, 7.8 mmol) were dissolved in p-dioxane (40 mL). The mixture was heated in a sealed tube under microwave irradiation at 120° C. for 15 minutes The solution was concentrated, and the residue was purified by chromatography over silica gel eluted with 1:1 ethyl acetate/hexanes to give 2-[(S)-2-tert-butoxycarbonylamino-3-(2-cyano-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester as a white solid (3.2 g, 95%).

Workup

  1. concentrationwas concentrated
  2. customthe residue was purified by chromatography over silica gel
  3. washeluted with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9504969f7aa04e3eb482a85ea209c27f
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

Loading…