Potassium tert-butoxide → (R,R)-N-[3-[4-(1,1-difluoroethyl)phenyl]isothiazol-5-yl]-2-methylcyclopropane-carboxamide

HRID 2422713Notes

Reaction equation

HRID 2422713 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([NH2:16])[S:13][N:12]=2)=[CH:7][CH:6]=1)([F:4])[CH3:3].[CH3:17][C@@H:18]1[CH2:20][C@H:19]1[C:21](OCC1C=CC=CC=1)=[O:22].CC(C)([O-])C.[K+]>C([O-])(O)=O.[Na+]>[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([NH:16][C:21]([C@@H:19]3[CH2:20][C@H:18]3[CH3:17])=[O:22])[S:13][N:12]=2)=[CH:7][CH:6]=1)([F:4])[CH3:3]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 67180743(1R,2r)-benzyl2-methylcyclopropanecarboxylateHCID 671825233-[4-(1,1-Difluoroethyl)phenyl]isothiazol-5-ylamine

Product 1

HCID 67182385(R,R)-N-[3-[4-(1,1-difluoroethyl)phenyl]isothiazol-5-yl]-2-methylcyclopropane-carboxamideYield 50.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Mix 3-[4-(1,1-difluoroethyl)phenyl]isothiazol-5-ylamine (0.200 g, 0.833 mmol), benzyl (R,R)-2-methylcyclopropanecarboxylate (0.238 g, 1.250 mmol) and potassium t-butoxide (0.190 g, 1.667 mmol) for 1 h. Dilute with satd NaHCO3 and extract with EtOAc. Wash the organic phase with brine, dry (MgSO4) and evaporate. Chromatography on silica gel, eluting with 10% EtOAc in CHCl3, affords (R,R)—N-[3-[4-(1,1-difluoroethyl)phenyl]isothiazol-5-yl]-2-methylcyclopropane-carboxamide. Yield: 50.3%. ES-MS: m/e 323.3 (m+1).

Workup

  1. extractionextract with EtOAc
  2. washWash the organic phase with brine
  3. dry with materialdry (MgSO4)
  4. customevaporate
  5. washChromatography on silica gel, eluting with 10% EtOAc in CHCl3

Sources & evidence

ORD record
ord-8f49d3697bc849b79217b286ab4b7a79
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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