Pyridine → HCID 178442984, compound

HRID 1586938Notes

Reaction equation

[CH:1]1[N:5]([CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:4]2[N:11]=[C:12]([NH2:16])[N:13]=[C:14]([OH:15])[C:3]=2[N:2]=1.N1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:22]=[CH:21]\[CH2:20]/[CH:19]=[CH:18]\[CH2:22]/[CH:21]=[CH:20]\[CH2:19][CH2:18][CH2:4][CH2:3][C:14]([O:10][CH2:9][CH2:8][O:7][CH2:6][N:5]1[C:4]2[NH:11][C:12]([NH2:16])=[N:13][C:14](=[O:15])[C:3]=2[N:2]=[CH:1]1)=[O:15]

Participants

Reactant 2

HCID 1049Pyridine

HCID 178508933HCID 178508933, compound2×

Product 1

HCID 178442984HCID 178442984, compound

Procedure

Acyclovir (ACV, 0.5 g, 2.22 mmol, used as a dry white powder) was suspended in anhydrous pyridine (10 ml) and to the mixture stirred under dry nitrogen was added GLA acid chloride (0.788 g, 2.664 mmol). The reaction mixture was stirred overnight at room temperature after which period TLC indicated conversion to the required product. The pyridine was removed in vacuo and the residual syrup was dissolved in chloroform. This was introduced into a column of silica gel (30 g) pre-equilibrated in chloroform:ethanol (30:1, v:v). Elution with chloroform followed by chloroform:ethanol (30:1), (20:1) and finally (15:1), gave the required product, AK-5, as a TLC homogeneous semisolid. Yield, 48% (0.517 g, 1.065 mmol).

Workup

stirringThe reaction mixture was stirred overnight at room temperature after which period TLC

Sources & evidence

ORD record: ord-56b823a720924ef3bd81830fd10b3c88
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05216142

Reaction notes

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