Hydrochloric Acid → HCID 178432750, compound

HRID 872069Notes

Reaction equation

C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].[Cl:9][CH:10]([C:15](=O)[CH3:16])[C:11](OC)=[O:12].Cl>CO.CCOCC>[Cl:9][C:10]1[C:11]([OH:12])=[N:7][C:5]([CH3:6])=[N:8][C:15]=1[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium methoxide (328 mg, 6.08 mmol, 30% solution in MeOH) was added to a stirring suspension of acetamidine hydrochloride (191 mg, 2.03 mmol) and methyl 2-chloro-3-oxobutanoate (500 mg, 3.04 mmol) in MeOH (10.1 mL). The reaction mixture was heated to 80° C. for 3 hours and then cooled to room temperature. With stirring, the reaction was treated with 2N HCl in Et2O (50 mL), and then concentrated in vacuo. The resulting solid was suspended in 1:1 acetone/CH2Cl2, stirred vigorously for 10 mins, and the solids collected by filtration to afford the title compound as a light yellow solid. The isolated product was sufficiently pure to use in the subsequent step without further purification. LRMS m/z (M+H) 159.2 found, 159.0 required.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
stirringstirred vigorously for 10 mins
filtrationthe solids collected by filtration

Sources & evidence

ORD record: ord-8af6867226f24b7ba9bee27f4950e6ff
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975261B2

Reaction notes

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