Dichloromethane → HCID 57948923, compound

HRID 1992283Notes

Reaction equation

HRID 1992283 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH2:15])([CH2:11][C:12]([CH3:14])=[CH2:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:15][C:25]([NH:24][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[S:26])([CH2:11][C:12]([CH3:14])=[CH2:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68284Benzoyl isothiocyanateHCID 57948940HCID 57948940, compound

Product 1

HCID 57948923HCID 57948923, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(3-bromo-4-fluorophenyl)-4-methylpent-4-en-2-amine (1.3 g, 4.6 mmoles, 1.0 equiv) in THF (5 mL) is added benzoyl isothiocyanate (0.63 mL, 4.6 mmoles, 1 equiv). The reaction is stirred at room temperature for 3 h. The solvent is removed under reduced pressure and the residue is purified by silica gel chromatography eluting with a linear gradient of 20% dichloromethane: hexanes to 50% dichloromethane: hexanes to give the title compound (84% yield): MS (m/z): 457, 459 (M+23).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by silica gel chromatography
  3. washeluting with a linear gradient of 20% dichloromethane

Sources & evidence

ORD record
ord-2f83a164acc5434eaeba5114ef0e35ee
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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