Carbonic acid, bis(1,1-dimethylethyl) ester → 2-Tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole

HRID 49137Notes

Reaction equation

HRID 49137 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH2:13][C:14]1[S:15][C:16]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:21]=2)=[CH:17][N:18]=1>C1COCC1>[CH3:29][O:28][C:26](=[O:27])[C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:19][C:16]2[S:15][C:14]([NH:13][C:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])=[N:18][CH:17]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 222883712-Amino-5-[(3-carbomethoxyphenyl)thio]thiazole

Product 1

HCID 221704102-Tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-t-butylcarbonate (4.36 g, 20 mmol) was added to a stirred solution of 2-amino-5-[(3-carbomethoxyphenyl)thio]thiazole (1.33 g, 5 mmol) and 4-N,N-dimethylaminopyridine (62 mg, 0.5 mmol) in THF (120 mL). The solution was stirred at rt. for 6 h and concentrated. The residue was purified using flash column chromatography on silica gel. Elution with 10% EtOAc in hexanes followed by 25% EtOAc in hexanes afforded a mixture of the titled compound and the corresponding bis(tert-butoxycarbonyl)amino adduct (1.8 g) as an oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified
  3. washElution with 10% EtOAc in hexanes
  4. customafforded

Sources & evidence

ORD record
ord-4e312f34438e490a9dd251549b6ba075
Source dataset
uspto-grants-2004_03
Patent number
US06706717B2

Reaction notes

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