Cidofovir → Hpmpc diea

HRID 560966

Reaction equation

HRID 560966 reaction equation
[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5].[CH:10]1[C:16]([NH2:17])=[N:15][C:13](=[O:14])[N:12]([CH2:18][C@H:19]([O:22][CH2:23][P:24]([OH:27])([OH:26])=[O:25])[CH2:20][OH:21])[CH:11]=1>CN(C=O)C>[CH:10]1[C:16]([NH2:17])=[N:15][C:13](=[O:14])[N:12]([CH2:18][C@H:19]([O:22][CH2:23][P:24]([OH:27])([OH:26])=[O:25])[CH2:20][OH:21])[CH:11]=1.[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 60613CidofovirHCID 81531Diisopropylethylamine

Product 1

HCID 131727369Hpmpc diea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 mL of DMF and 400 μL of DIEA was added to 200 mg (0.63 mmol) HPMPC to produce a HPMPC-DIEA salt. Solvent was removed under vacuo and HPMPC-DIEA salt was carefully dried. 1.5 times excess of desired dipeptide from the general procedure described above was added to the dry HPMPC-DIEA salt, as well as 7 mL dry DMF and 400 μL DIEA. The mixture was heated for 1 h at 40° C. before 660 mg (1.3 mmol) PyBOP was added. Reaction was monitored by 31P NMR, and additional portions of PyBOP were added until the reaction was completed. Solvent was removed under vacuo, and purified by silica gel column chromatography [Solvent system: (CH2Cl2), (CH2Cl2: acetone, 2:1), (CH2Cl2: acetone: MeOH, 20:10:3)].

Sources & evidence

ORD record
ord-c78d0168f3fd4f69b75d2d10a111ac83
Source dataset
uspto-grants-2011_11
Patent number
US08063209B2

Linked notes

Loading…