Methanol → HCID 136461733, compound

HRID 1168584Notes

Reaction equation

HRID 1168584 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:31])[C:10]2[N:11]=[CH:12][N:13]([C:29]=2[N:30]=1)[C@@H:14]1[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:15]1[O:16][CH2:17][CH2:18][O:19][N:20]([CH3:22])[CH3:21])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:32](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:41]1[CH:48]=[CH:47][C:44]([O:45][CH3:46])=[CH:43][CH:42]=1)[C:33]1[CH:40]=[CH:39][C:36]([O:37][CH3:38])=[CH:35][CH:34]=1.CO>N1C=CC=CC=1.CCOC(C)=O.CN(C1C=CC=CN=1)C>[CH3:46][O:45][C:44]1[CH:43]=[CH:42][C:41]([C:32]([O:27][CH2:26][C@H:25]2[O:28][C@@H:14]([N:13]3[C:29]4[N:30]=[C:7]([NH:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[NH:8][C:9](=[O:31])[C:10]=4[N:11]=[CH:12]3)[C@H:15]([O:16][CH2:17][CH2:18][O:19][N:20]([CH3:22])[CH3:21])[C@@H:23]2[OH:24])([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:33]2[CH:40]=[CH:39][C:36]([O:37][CH3:38])=[CH:35][CH:34]=2)=[CH:48][CH:47]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)2×HCID 136461725HCID 136461725, compound

Product 1

HCID 136461733HCID 136461733, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N2-isobutyryl-2′-O-(dimethylaminooxyethyl) guanosine (42.63 g, 27.44 mmol) and dimethylaminopyridine (168 mg, 1.37 mmol) dissolved in anhydrous pyridine (274 mL) was added DMT-Cl (9.30 g, 27.44 mmol). After several hours additional DMT-Cl (9.30 g, 27.44 mmol) was added. After several more hours MeOH (22 mL, 543 mmol) was added, and the reaction mixture was stirred for 30 minute. The solvent was evaporated in vacuo to give an oil which was dissolved in EtOAc (550 mL). The resulting suspension was washed with a mixture of H2O (50 mL) and brine (25 mL) twice, then with brine (50 mL). NEt3 (5 mL) was added, the organic phase was dried with MgSO4 and the solvent was evaporated in vacuo to give a foam. The foam was purified by column chromatography (silica pretreated with 1% NEt3) using CH2Cl2-EtOAc-MeOH-NEt3, 75:25:10:1, to afford the title compound as a foam (16.3 g, 80%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil which
  3. washThe resulting suspension was washed with a mixture of H2O (50 mL) and brine (25 mL) twice
  4. additionNEt3 (5 mL) was added
  5. dry with materialthe organic phase was dried with MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customto give a foam
  8. customThe foam was purified by column chromatography (silica pretreated with 1% NEt3)

Sources & evidence

ORD record
ord-5aaff616ea70481f8c801bc2b261ea4e
Source dataset
uspto-grants-2003_09
Patent number
US06624294B2

Reaction notes

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