Dimethylformamide → N,N,N',N'-Tetramethylazodicarboxamide

To the solution of acid (63) (330 mg, 0.74 mmol) in CH2Cl2 (10 mL) was added oxalyl chloride (77 μL, 0.88 mmol) and the catalytic amount of DMF. The reaction mixture was stirred for 1 hr and concentrated in vacuo. The residue (crude acyl chloride) was diluted with CH2Cl2 (10 mL) and pivalohydrazide (128 mg, 1.10 mmol) and triethylamine (0.31 mL, 2.21 mmol) was added. The reaction mixture was stirred for 2 hrs at room temperature. The reaction mixture was concentrated in vacuo and diluted with EtOAc (50 mL). The organic layer was washed with aq. 1N HCl and aq. sat'd NaHCO3 solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by Prep-LC (Gilson) provided 244 mg (61%) of desired diamide as solid.

1. concentrationconcentrated in vacuo
2. additionwas added
3. stirringThe reaction mixture was stirred for 2 hrs at room temperature
4. concentrationThe reaction mixture was concentrated in vacuo
5. additiondiluted with EtOAc (50 mL)
6. washThe organic layer was washed with aq. 1N HCl and aq. sat'd NaHCO3 solution
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by Prep-LC (Gilson)

ORD record

ord-55edbabeaad54a1ab3564d665f61bf4d

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875647B2