Ethyl Acetate → HCID 86599741, compound

HRID 2252704Notes

Reaction equation

HRID 2252704 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C@@H:14]([OH:15])[C@@:12]3([CH3:27])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.COC1C=CC([C:36](Cl)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=CC=1.[C:50]([O:53][CH2:54][CH3:55])(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:50][O:53][C:54]1[CH:55]=[CH:9][C:10]([N:1]([CH:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:2]2[C:3]3[CH:10]=[CH:9][N:8]([C@@H:11]4[O:17][C@H:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[C@@H:14]([OH:15])[C@@:12]4([CH3:27])[OH:13])[C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 84462p-(Chlorodiphenylmethyl)anisoleHCID 59645177HCID 59645177, compound

Product 1

HCID 86599741HCID 86599741, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of the compound from Step G (394 mg, 1.0 mmol) in anhydrous pyridine (5 mL) was added p-methoxyphenylchlorodiphenylmethane (946 mg, 3.06 mmol) and 4-dimethylaminopyridine (DMAP) (123 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 20 h. It was then diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate solution (3×15 mL) followed by water (2×15mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to an oil. The crude product was purified using column chromatography on silica gel eluting with 5% MeOH in CH2Cl2. The appropriate fractions were collected and evaporated to give the title compound (540 mg).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (3×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated to an oil
  4. customThe crude product was purified
  5. customThe appropriate fractions were collected
  6. customevaporated

Sources & evidence

ORD record
ord-d63e324235c7415ebb2d4693e53240c9
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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