1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl Ester

HRID 20902

반응식

HRID 20902 반응식
[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH:20]([OH:22])[CH2:19][CH:18]1[CH2:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](Cl)(C1C=CC=CC=1)([C:35]1[CH:42]=[CH:41][C:38]([O:39][CH3:40])=[CH:37][CH:36]=1)[C:27]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[CH:29][CH:28]=1>N1C=CC=CC=1.CN(C1C=CC=CN=1)C>[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH:20]([OH:22])[CH2:19][CH:18]1[CH:23]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:24][CH:26]([C:27]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[CH:29][CH:28]=1)[C:35]1[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[CH:41][CH:42]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 72260745[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-hexyl]-carbamic Acid Benzyl Ester

생성물 1

HCID 131728214(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl Ester수율 436.1%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 1049Pyridine용매2회

실험 절차

Compound 29 (6 g, 17 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (60 mL). To this solution dimethylamino pyridine (0.207 g, 1.7 mmol) and DMT-Cl (6 g, 17.9 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. The excess DMT-Cl was quenched by the addition of methanol (25 mL). The solution was dried under reduced pressure. To the residue was suspended in ethyl acetate (300 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. 24.2 g of the crude product was obtained after removal of the solvent. Upon purification over silica gel using 2% MeOH/DCM compound 30 (8.7 g, 79%) was obtained as white foamy solid.

후처리

  1. customThe excess DMT-Cl was quenched by the addition of methanol (25 mL)
  2. customThe solution was dried under reduced pressure
  3. washwashed with saturated bicarbonate solution, brine and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-68a52cdc6d394e3198a123be1371cd77
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745608B2

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