Acetic Acid → Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

HRID 2075956ノート

反応式

HRID 2075956 の反応式
[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N+:29]#[C-:30])([CH3:28])([CH3:27])[CH3:26].[C:31](O)(=[O:33])[CH3:32].C(#N)C.[OH2:38]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:14]([O:15][C:31](=[O:33])[CH3:32])[C:30](=[O:38])[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 962WaterHCID 6342AcetonitrileHCID 23577Tert-Butyl isocyanideHCID 595656495-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde

生成物 1

HCID 86647228Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde (Reference example 15-1) (453 mg), tert-butylisocyanide (465 mg), acetic acid (0.32 mL) and acetonitrile (8 mL) was stirred at 70° C. for 13 hours. After cooling to room temperature, ethyl acetate and water were added to the mixture. The separated organic layer was washed with water, an aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution) to give the title compound (604 mg).

後処理

  1. temperatureAfter cooling to room temperature
  2. washThe separated organic layer was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution)

出典と根拠

ORDレコード
ord-725ea753136447e5be442f51724feb1e
出典データセット
uspto-grants-2011_04
特許番号
US07923462B2

反応ノート

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