2-Amino-thiazole-5-carboxylic acid ethyl ester → HCID 21094164, compound
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH2:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:23](O)=[O:24])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>>[CH3:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]([CH2:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:23]([NH:1][C:2]2[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=2)=[O:24])=[CH:20][CH:21]=1)(=[O:15])=[O:14]Participants
Procedure
Ethyl 2-aminothiazole-5-carboxylate (2.21 g, 12.8 mmol) was condensed with 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid (Preparation 41, 1.00 g, 3.2 mmol) using the procedure described for EXAMPLE 65, to give ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionylamino]thiazole-5-carboxylate: m/z (ES+)=508.3 [M+MeCN+H]+. LiOH.H2O (410 mg, 9.8 mmol) was added to a solution of this ester (1.44 g, 3.1 mmol) in THF-H2O (3:1, 30 mL). The mixture was stirred at 20° C. for 16 h and then at 55° C. for 24 h. The solvents were removed in vacuo, then the residue was dissolved in H2O (50 mL). The aqueous solution was washed with EtOAc (20 mL), before being acidified to pH 1 with 2M HCl and extracted with EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to give a solid that was recrystallised (EtOAc-MeOH) to give the title compound: RTA=29.5 min; m/z (ES+)=480.2 [M+MeCH+H]+.
Sources & evidence
- ORD record
- ord-e32dcd4dd3db4e699dee91458b746cb2
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582632B2
Reaction notes
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