1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (2R,3R)-1-(Bis(4-methoxyphenyl)(phenyl)methoxy)-2-((4-acetamido-2-oxo-pyrimidin-1(2H)-yl)methyl)butan-3-ol

HRID 1754606Notes

Reaction equation

HRID 1754606 reaction equation
[C:1](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:10]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=1)[C:2]1[CH:9]=[CH:8][C:5]([O:6][CH3:7])=[CH:4][CH:3]=1.[C:25]([NH:28][C:29]1[CH:34]=[CH:33][N:32]([CH2:35][C@@H:36]([C@H:39]([OH:41])[CH3:40])[CH2:37][OH:38])[C:31](=[O:42])[N:30]=1)(=[O:27])[CH3:26]>N1C=CC=CC=1>[CH3:7][O:6][C:5]1[CH:8]=[CH:9][C:2]([C:1]([C:10]2[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:38][CH2:37][C@@H:36]([CH2:35][N:32]2[CH:33]=[CH:34][C:29]([NH:28][C:25](=[O:27])[CH3:26])=[N:30][C:31]2=[O:42])[C@H:39]([OH:41])[CH3:40])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 90411135(2R,3R)-2-((4-Acetamido-2-oxo-pyrimidin-1(2H)-yl)methyl)butane-1,3-diol

Product 1

HCID 90413107(2R,3R)-1-(Bis(4-methoxyphenyl)(phenyl)methoxy)-2-((4-acetamido-2-oxo-pyrimidin-1(2H)-yl)methyl)butan-3-olYield 91.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

DMTCl (0.9 g, 2.66 mmol) was added to a stirred solution of 21 (0.6 g, 2.35 mmol) in 25 ml of anhydrous pyridine. After being stirred at room temperature for 4 hrs the reaction was quenched with MeOH (2 ml) and concentrated to an oil. The oil was partition between dichloromethane and 10% citric acid. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The resulting material was chromatographed on silica eluting with a gradient of methanol (5-7.5%) in ethyl acetate. Concentration of the pure product fractions afforded 1.2 g (91%) of 22 as a white amorphous solid. 1H NMR (DMSO-d6): δ 10.78 (s, 1H), 7.77 (d, J=7.2 Hz, 1H), 7.27 (m, 5H), 6.97 (d, J=7.2 Hz, 1H), 6.84 (m, 4H), 4.66 (d, J=4.8 Hz, 1H), 4.01 (m, 1H), 3.78 (m, 2H), 3.73 (s, 6H), 3.73 (m, 1H), 3.09 (m, 2.89 (m, 1H), 2.12 (m, 1H), 2.09 (s, 3H), 1.02 (d, J=6.3 Hz, 3H).

Workup

  1. customwas quenched with MeOH (2 ml)
  2. concentrationconcentrated to an oil
  3. customThe oil was partition between dichloromethane and 10% citric acid
  4. washThe organic phase was washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting material was chromatographed on silica eluting with a gradient of methanol (5-7.5%) in ethyl acetate

Sources & evidence

ORD record
ord-840709ca28d049f08794cbe350184a24
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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