Dicyclohexylcarbodiimide → HCID 53971898, 화합물

HRID 726946

반응식

HRID 726946 반응식
[F:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=O)[CH2:3]1.[OH-].[K+].[Cl:12][C:13]1[C:18]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:17][C:16]([N:23]=[C:24]=[S:25])=[C:15]([F:26])[CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>CO.O.C(#N)C>[Cl:12][C:13]1[C:18]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:17][C:16]([N:23]=[C:24]2[N:5]3[CH2:6][CH:2]([F:1])[CH2:3][CH:4]3[C:7](=[O:9])[S:25]2)=[C:15]([F:26])[CH:14]=1

참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 14797Potassium HydroxideHCID 136079331-Chloro-5-fluoro-4-isothiocyanato-2-[(propan-2-yl)oxy]benzeneHCID 222148884-Fluoro-L-proline

생성물 1

HCID 53971898HCID 53971898, 화합물수율 89.8%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 1.31 g (0.01 mol) 4-fluoroproline, 30 mL 2N KOH in methanol and 10 mL water is prepared before 2.46 g (0.01 mol) 4-chloro-2-fluoro-5-isopropoxy-phenylisothiocyanate dissolved in 250 mL methanol is added dropwise. The reaction mixture is stirred overnight at room temperature, the aqueous phase adjusted to pH 2 and the resultant product (3.77 g, See Formula X) is filtered. The compound thus obtained is dissolved in 50 mL acetonitrile before 2.59 g (0.01 mol) dicyclohexylcarbodiimide is added at room temperature. The reaction mixture is stirred for 3 h and the crude product is purified by silica gel chromatography to give 3.24 g (85% yield) of the desired product.

후처리

  1. additionis added dropwise
  2. filtrationthe resultant product (3.77 g, See Formula X) is filtered
  3. customThe compound thus obtained
  4. additionis added at room temperature
  5. stirringThe reaction mixture is stirred for 3 h
  6. customthe crude product is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-804654d342e24569ad4a9a350c28f6c9
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712225

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