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

HRID 1109953

반응식

HRID 1109953 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b8bae25343c46f4b7223d4db5d4d0e0
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324451

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