Methanol → HCID 136330638, compound

HRID 1858381Notes

Reaction equation

HRID 1858381 reaction equation
[C@@H:1]1([N:9]2[C:13]3[N:14]=[C:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[NH:16][C:17](=[O:18])[C:12]=3[C:11]([I:25])=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.[CH3:26][O:27][C:28]1[CH:49]=[CH:48][C:31]([C:32](Cl)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1.CO.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([C:32]([O:8][CH2:7][C@H:5]2[O:6][C@@H:1]([N:9]3[C:13]4[N:14]=[C:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[NH:16][C:17](=[O:18])[C:12]=4[C:11]([I:25])=[CH:10]3)[CH2:2][C@@H:3]2[OH:4])([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:31]2[CH:48]=[CH:49][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 136330639HCID 136330639, compound

Product 1

HCID 136330638HCID 136330638, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound (59) is repeatedly dried by evaporating off anhydrous pyridine. 400 mg (0.87 mmol) of compound (59) which has been dried in this way are dissolved in 5 ml of anhydrous pyridine. After adding 4,4'-dimethoxytrityl chloride (328 mg, 0.95 mmol) at room temperature, the reaction mixture is stirred overnight. MeOH (3 ml) and 5% aq. NaHCO3 (30 ml) are then added. The aqueous phase is extracted 3 times with CH2Cl2. The organic phase is dried (Na2SO4) and evaporated, and the residue is subjected to flash chromatography (column: 10×5 cm, solvent CH2Cl2 /acetone, 9:1). Isolating the material from the main zone affords the colorless, amorphous title compound (61). (600 mg, 91%). 1H-NMR ([D6 ] DMSO: δ=1.13 (m, 4 CH3), 2.24 (m, H--C(2')), 2.77 (m, CH), 3.12 (m, H--C(5')), 3.75 (s, 2 CH3O), 3.93 (m, H--C(4')), 4.35 (m, H--C(3')), 5.30 (d, 3'-OH), 6.39 (dd, H--C(1')), 6.86-7.39 (m, aromatic H +H--C(6)), 11.54, 11.82 (2s, 2 NH). Anal. calculated for C36H37JN4O7 (764.6): C, 56.55, H, 4.88, N, 7.33: found C, 56.42, H, 4.82, N, 7.30.

Workup

  1. dry with materialCompound (59) is repeatedly dried
  2. customby evaporating off anhydrous pyridine
  3. extractionThe aqueous phase is extracted 3 times with CH2Cl2
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. customevaporated
  6. customIsolating the material from the main zone

Sources & evidence

ORD record
ord-228183850090488ca9c9b2e23bea7792
Source dataset
uspto-grants-2000_11
Patent number
US06150510

Reaction notes

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