Diethyl Ether → 4-[(S)-2-methylbutoxycarbonyl]phenyl 4-[(S)-2-propoxypropanoyloxy]benzoate

HRID 1109953

反応式

HRID 1109953 の反応式
[CH2:1]([O:4][C@@H:5]([CH3:18])[C:6]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)=[O:7])[CH2:2][CH3:3].[CH3:19][C@@H:20]([CH2:32][CH3:33])[CH2:21][O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)=[O:24].C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:4][C@@H:5]([CH3:18])[C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:28]2[CH:29]=[CH:30][C:25]([C:23]([O:22][CH2:21][C@@H:20]([CH3:19])[CH2:32][CH3:33])=[O:24])=[CH:26][CH:27]=2)=[O:14])=[CH:16][CH:17]=1)=[O:7])[CH2:2][CH3:3]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 13530950Benzoic acid, 4-hydroxy-, (2S)-2-methylbutyl esterHCID 147935344-[(S)-2-Propoxypropanoyloxy]benzoic acid

生成物 1

HCID 148487874-[(S)-2-methylbutoxycarbonyl]phenyl 4-[(S)-2-propoxypropanoyloxy]benzoate収率 74.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

In 12 ml of methylene chloride were dissolved 107 mg of 4-[2-(S)-propoxypropanoyloxy]benzoic acid, 95 mg of 4-[(S)-2-methyl butoxycarbonyl]phenol, and 140 mg of dicyclohexylcarbodiimide, and a catalytic amount of 4-dimethylaminopyridine was added to the solution, followed by stirring at room temperature. After 5 hours, diethyl ether was added to the reaction mixture, and any insoluble matter was removed by filtration. The filtrate was washed successively with a 10% hydrochloric acid aqueous solution, a saturated sodium bicarbonate aqueous solution, water, and a saturated sodium chloride aqueous solution, and dried over sodium sulfate. The solvent was removed from the residue by distillation, and the resulting oily substance was purified by silica gel column chromatography to obtain 139 mg of the entitled compound as a transparent oily substance. This compound did not crystalize even when allowed to stand at room temperature or less for a long time. The structure of the compound was confirmed by NMR and IR spectra.

後処理

  1. customany insoluble matter was removed by filtration
  2. washThe filtrate was washed successively with a 10% hydrochloric acid aqueous solution
  3. dry with materiala saturated sodium bicarbonate aqueous solution, water, and a saturated sodium chloride aqueous solution, and dried over sodium sulfate
  4. customThe solvent was removed from the residue by distillation
  5. customthe resulting oily substance was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4b8bae25343c46f4b7223d4db5d4d0e0
出典データセット
uspto-grants-1994_06
特許番号
US05324451

関連ノート

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