BOC-2-AMINO-4-THIAZOLE-CARBOXYLIC ACID

General procedure: An aqueous KOH (10percent w/v) solution was added to an ester solution in THF. The reaction mixture was stirred at room temperature until reagent disappearance was confirmed by TLC. HCl 1 M was added until pH 4 and the solution was extracted with EtOAc.The organic layer was dried over MgSO4 and concentrated in vacuoto afford the acid.(2) A mixture of compound 2 (11.5 g, 42.3mmol), NaOH (3.4 g, 84.6 mol) and HTo a solution of methyl 2-[[(tert-butoxy)carbonyl]amino]-l, 3-thiazole-4-carboxylate (28 g, 108 mmol) in tetrahydrofuran (300 mL) was added a solution of lithium hydroxide (10.4 g, 433 mmol) in water (150 mL). The resulting mixture was stirred for 12 h at room temperature. The pH of the solution was adjusted to 4 with hydrochloric acid (2 mol/L). The solids were collected by filtration to afford 2- [[(teri-butoxy)carbonyl]amino]-l, 3-thiazole-4-carboxylic acid (20 g, 76percent) as an off-white solid. LCMS (ESI): M+H2-tert-Butoxycarbonylamino-thiazole-4-carboxylic acid methyl ester (15.5 g, 60.01 mmol) was dissolved in 4:1 tetrahydrofuran:water (300 mL) followed by the addition of lithium hydroxide monohydrate (5.29 g, 126.07 mmol). The solution was stirred overnight at room temperature. Tetrahydrofuran was removed under vacuum and the salt was neutralized with 2.0 N aqueous hydrochloric acid. The resulting precipitate was filtered and dried to give 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (10.4 g, 71percent).

Molecular Weight:244.27
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:244.05177804
Monoisotopic Mass:244.05177804
Topological Polar Surface Area:117
Heavy Atom Count:16
Complexity:290
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes