METHYL 2-((TERT-BUTOXYCARBONYLAMINO)METHYL)OXAZOLE-4-CARBOXYLATE synthesis

9synthesis methods

Product Name:METHYL 2-((TERT-BUTOXYCARBONYLAMINO)METHYL)OXAZOLE-4-CARBOXYLATE
CAS Number:182120-89-4
Molecular formula:C11H16N2O5
Molecular Weight:256.26

4-Oxazolecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4,5-dihydro-, methyl ester

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METHYL 2-((TERT-BUTOXYCARBONYLAMINO)METHYL)OXAZOLE-4-CARBOXYLATE

182120-89-4
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Yield:182120-89-4 130 mg

Reaction Conditions:

with Bromotrichloromethane;1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane at 0 - 25; for 12 h;Inert atmosphere;

Steps:

2 Step 3:

a solution of intermediate 3 (254 mg, 0.98 mmol) in DCM (24 mL) was added to BrCCb (0.7 mL, 2.94 mmol) at 0 °C. The mixture was stirred at 0 °C for 5 minutes before DBU (1.13 mL, 2.94 mmol) was added drop-wisely over 2 minutes. The mixture was stirred at 25 °C for 12 hours before quenched with ice-cooled aq.NaHCCh solution and extracted with DCM twice. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel (PE: EtOAc= 3 : 1) to give intermediate 4 (130 mg, yield 60.7%) as yellow oil. LC/MS (ESI) (m/z): 257 (M+H)+.

References:

WO2020/198062,2020,A1 Location in patent:Page/Page column 336-338