Pyridine → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester

HRID 1055773

反応式

HRID 1055773 の反応式
[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH2:24][OH:25])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32]N=1)C.[C:36](Cl)(C1C=CC=CC=1)([C:45]1[CH:52]=[CH:51][C:48]([O:49][CH3:50])=[CH:47][CH:46]=1)[C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1.N1C=CC=C[CH:61]=1>>[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH:24]([C:32]1[CH:61]=[CH:30][CH:35]=[CH:34][CH:33]=1)[O:25][CH:36]([C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1)[C:45]1[CH:46]=[CH:47][C:48]([O:49][CH3:50])=[CH:51][CH:52]=1)=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 1049Pyridine2 回HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 68638015[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

生成物 1

HCID 131728206(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester

実験手順

Referring to scheme 1, compound 3a (14 g, 38.4 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (60 mL). To this solution dimethylamino pyridine (0.488 g, 4 mmol) and DMT-Cl (13.6 g, 40.3 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 4a (21.3 g, 83%) was obtained as white foamy solid.

後処理

  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

出典と根拠

ORDレコード
ord-f746b6152fcd4a5083caf7e616a302ac
出典データセット
uspto-grants-2016_07
特許番号
US09394540B2

関連ノート

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