Dicyclohexylcarbodiimide → HCID 53971898, compound

HRID 726946

Reaction equation

HRID 726946 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 53971898HCID 53971898, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-804654d342e24569ad4a9a350c28f6c9
Source dataset
uspto-grants-1998_01
Patent number
US05712225

Linked notes

Loading…