Potassium Carbonate → 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxy-butyric acid 3,4-methylenedioxybenzyl ester

HRID 1760819ノート

反応式

HRID 1760819 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:13][C@H:14]([C@@H:18]([OH:20])[CH3:19])[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[C:5]([CH3:21])[C:4]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].[CH2:29]1[O:39][C:38]2[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][C:31]=2[O:30]1.[I-].[Li+]>CN(C)C=O.C(Cl)Cl>[CH2:29]1[O:39][C:38]2[CH:37]=[CH:36][C:33]([CH2:34][O:16][C:15](=[O:17])[C@H:14]([NH:13][S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:22])[C:5]=3[CH3:21])(=[O:11])=[O:12])[C@@H:18]([OH:20])[CH3:19])=[CH:32][C:31]=2[O:30]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 183375572(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxybutyric acid

生成物 1

HCID 865900252(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxy-butyric acid 3,4-methylenedioxybenzyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxybutyric acid (29.13 g, 87.9 mmol) in dimethylformamide (280 mL) at 0° C., was added potassium carbonate (72.9 g, 527 mmol) and a solution of 3,4-methylenedioxybenzyl chloride ((60 g, 170.8 mmol, 50% (w/w)) in methylene chloride. After 2 h, lithium iodide (5.88 g, 44 mmol) was added and the reaction mixture was warmed to rt. over 2 h. After 6 h, the reaction mixture was partitioned between ethyl acetate (600 mL) and water (250 mL). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. The crude residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes) to afford 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxybutyric acid 3,4-methylenedioxybenzyl ester (40.4 g), a portion which was taken directly into the next reaction without further purification.

後処理

  1. waitover 2 h
  2. waitAfter 6 h
  3. customthe reaction mixture was partitioned between ethyl acetate (600 mL) and water (250 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-6a551b14088e48f4adc59ce8e3b51221
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

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