N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-din-octanoyloxy-2-propoxymethyl)guanine → 9-(1,3-Di-n-octanoyloxy-2-propoxymethyl)guanine

HRID 65108Notes

Reaction equation

HRID 65108 reaction equation
N#N.COC1C=CC(C([NH:24][C:25]2[NH:26][C:27](=[O:59])[C:28]3[N:29]=[CH:30][N:31]([CH2:34][O:35][CH:36]([CH2:48][O:49][C:50](=[O:58])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:37][O:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:32]=3[N:33]=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)(=O)C.O>[C:39]([O:38][CH2:37][CH:36]([O:35][CH2:34][N:31]1[CH:30]=[N:29][C:28]2[C:27](=[O:59])[NH:26][C:25]([NH2:24])=[N:33][C:32]1=2)[CH2:48][O:49][C:50](=[O:58])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])(=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

4

Reactant 1

HCID 136332157N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-din-octanoyloxy-2-propoxymethyl)guanine

Product 1

HCID 1363321599-(1,3-Di-n-octanoyloxy-2-propoxymethyl)guanineYield 63.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 0.969 g of N2 -(4-methoxyphenyldiphenylmethyl)-9-(1,3-di-n-octanoyloxy-2-propoxymethyl)guanine in 40 ml of glacial acetic acid plus 10 ml of water was stirred at 75° C. for 3 hours. The solution was then concentrated and the residue chromatographed over silica gel eluting with 1:15 methanol:methylene chloride to give a white solid. The product was recrystallized from methanol to afford 0.385 g of 9-(1,3-di-n-octanoyloxy-2-propoxymethyl)guanine, m.p. 165°-166° C.

Workup

  1. concentrationThe solution was then concentrated
  2. customthe residue chromatographed over silica gel eluting with 1:15 methanol
  3. custommethylene chloride to give a white solid
  4. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-26c19f5cba6e4a4587b94939921dde64
Source dataset
uspto-grants-1986_09
Patent number
US04612314

Reaction notes

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