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

HRID 1655344Notes

Reaction equation

HRID 1655344 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:24][C:25]2[NH:26][C:27](=[O:41])[C:28]3[N:29]=[CH:30][N:31]([CH2:34][O:35][CH:36]([CH2:39][OH:40])[CH2:37][OH:38])[C:32]=3[N:33]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[C:42](Cl)(=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].[OH2:52]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)Cl>[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH:24][C:25]2[NH:26][C:27](=[O:41])[C:28]3[N:29]=[CH:30][N:31]([CH2:34][O:35][CH:36]([CH2:37][O:38][C:9](=[O:52])[CH2:10][CH2:5][CH2:6][CH2:7][CH2:8][CH2:11][CH3:12])[CH2:39][O:40][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:32]=3[N:33]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 962WaterHCID 8124Octanoyl chlorideHCID 136387272N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-dihydroxy-2-propoxymethyl)guanine

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 1.05 g of N2 -(4-methoxyphenyldiphenylmethyl)-9-(1,3-dihydroxy-2-propoxymethyl)guanine and 25 mg of 4-dimethylaminopyridine in 30 ml of dry pyridine was added dropwise a solution of 1.2 g of n-octanoyl chloride in 10 ml of methylene chloride. After 15 hour, 1.5 ml of water was added and the solution concentrated at reduced pressure. The residue was chromatographed over silica gel eluting with 1:9 methanol:methylene chloride to give a white solid which was recrystallized from ethyl acetate:hexane to N2 -(4-methoxyphenyldiphenylmethyl)-9-(1,3-di-n-octanoyloxy-2-propoxymethyl)guanine.

Workup

  1. concentrationthe solution concentrated at reduced pressure
  2. customThe residue was chromatographed over silica gel eluting with 1:9 methanol
  3. custommethylene chloride to give a white solid which
  4. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b91386d23efb488493dbd1614db3ad71
Source dataset
uspto-grants-1993_10
Patent number
US05250535

Reaction notes

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