Pentane → Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

HRID 520486

Reaction equation

HRID 520486 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[C:12](=O)([O:18]C(C)(C)C)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].CCCCC>C1COCC1.CN(C)C1C=CN=CC=1>[C:14]([O:13][C:12]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8003PentaneHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylateYield 66.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-aminothiazole-4-carboxylate 87 (10.0 g, 58.1 mmol) was taken up in 150 mL of anhydrous THF along with di-tert-butyl carbonate (12.67 g, 58.1 mmol) and 4-(dimethyl)aminopyridine (DMAP) (10 mg, 0.082 mmol). The reaction mixture was stirred at 50° C. for 4 h and then at room temperature for 18 h. It was then concentrated under reduced pressure to obtain a thick oil. Pentane was added and the resulting crystalline materials were collected by filtration and dried to afford 88 (10.5 g, 66% yield).

Workup

  1. waitat room temperature for 18 h
  2. concentrationIt was then concentrated under reduced pressure
  3. customto obtain a thick oil
  4. filtrationthe resulting crystalline materials were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-a3d6ca76c1374673babeeba4ad81903f
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Linked notes

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