Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate–succinic acid (2/1)
نویسندگان
چکیده
The title compound, C(20)H(32)N(5)O(8)P·0.5C(4)H(6)O(4), is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N-H⋯O and SA-AD O-H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N-H⋯O-P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) Å] between adjacent inversion-related adenine groups.
منابع مشابه
Diisopropyl {[(R)-2-(2-amino-6-chloro-9H-purin-9-yl)-1-methylethoxy]methyl}phosphonate
In the title compound, C(15)H(25)ClN(5)O(4)P, the r.m.s. deviation for the purine ring system is 0.0165 Å. The coordination about the P atom is a distorted tetrahedron [O=P-O angles = 116.70 (6) and 109.87 (6)°]. In the crystal, molecules are linked by N-H⋯O hydrogen bonds, generating a three-dimensional network.
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The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, a minor impurity of acyclovir, is described. Starting with commercial N-(9-acetyl-6-oxo-1H-purin-2-yl)acetamide, the process uses an acid catalysed phase transfer catalysis (PTC) process to produce the selective alkylation at the 9 position of the guanine ring.
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عنوان ژورنال:
دوره 68 شماره
صفحات -
تاریخ انتشار 2012