Dimethylformamide → HCID 59186683, compound

HRID 731536Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([O:20][CH3:21])[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.C(Cl)(=O)C(Cl)=O.C[N:33](C=O)C>ClCCl>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([O:20][CH3:21])[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:33])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of EXAMPLE 1E in dichloromethane (20 mL) was treated with oxalyl chloride (0.305 mL, 3.50 mmol) and a drop of DMF, stirred for 6 hours at room temperature, and concentrated. The resulting residue was dissolved in dichloromethane (20 mL), cooled to 0° C., treated with aqueous NH3 (3 mL), stirred for 6 hours, and partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4) and filtered. Concentration of the filtrate gave the desired product as a residue that was utilized directly in the next step without further purification. MS

Workup

concentrationconcentrated
dissolutionThe resulting residue was dissolved in dichloromethane (20 mL)
additiontreated with aqueous NH3 (3 mL)
custompartitioned between ethyl acetate and saturated aqueous sodium chloride
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate three times
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered

Sources & evidence

ORD record: ord-161c3b253c864e6da3777c951329dd46
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585858B2

Reaction notes

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