Sodium Bicarbonate → HCID 67452133, compound

HRID 1519236Notes

Reaction equation

HRID 1519236 reaction equation
Cl.[CH:2]1([C:5](=[NH:8])[O:6][CH3:7])[CH2:4][CH2:3]1.Cl.N[CH:11](CO)[C:12]([O:14][CH3:15])=[O:13].C(=O)(O)[O-].[Na+]>ClCCl>[CH:2]1([C:5]2[O:6][CH2:7][CH:11]([C:12]([O:14][CH3:15])=[O:13])[N:8]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517373Methyl DL-serinate hydrochlorideHCID 13928570Methyl cyclopropanecarboximidate--hydrogen chloride (1/1)

Product 1

HCID 67452133HCID 67452133, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 500-mL 3-necked round-bottom flask were placed methyl cyclopropanecarbimidate hydrochloride (13.6 g, 100.00 mmol, 1.00 equiv.), methyl 2-amino-3-hydroxypropanoate hydrochloride (17.6 g, 112.82 mmol, 1.10 equiv.) and dichloromethane (150 mL). The resulting solution was stirred for 24 hours at room temperature, then added sodium bicarbonate (16.8 g, 200.00 mmol, 2.00 equiv.). The resulting solution was stirred for 24 hours at room temperature. The solid was filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2). This resulted in 8 g (47% yield) of methyl 2-cyclopropyl-4,5-dihydrooxazole-4-carboxylate as a colorless oil.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask were placed
  2. stirringThe resulting solution was stirred for 24 hours at room temperature
  3. filtrationThe solid was filtered out
  4. concentrationThe filtrate was concentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether (1:2)

Sources & evidence

ORD record
ord-2fc528922b3440938e6d57655521e49a
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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