Potassium Carbonate → Ethyl 3-[3-((1S)-2-{[2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amino}-1-hydroxyethyl)-4,5-difluorophenyl]propanoate

HRID 602043Notes

Reaction equation

HRID 602043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[C:6]([C@H:9]([OH:12])[CH2:10]I)[C:7]=1[F:8].[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH:21]1[CH2:29][C:30]([NH2:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH:21]1[CH2:29][C:30]([NH:33][CH2:10][C@H:9]([C:6]1[CH:5]=[C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=[C:2]([F:1])[C:7]=1[F:8])[OH:12])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98341731-(2,3-Dihydro-1H-inden-2-yl)-2-methylpropan-2-amineHCID 68794275Ethyl 3-{3,4-difluoro-5-[(1S)-1-hydroxy-2-iodoethyl]phenyl}propanoate

Product 1

HCID 24957326Ethyl 3-[3-((1S)-2-{[2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amino}-1-hydroxyethyl)-4,5-difluorophenyl]propanoateYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 3-{3,4-difluoro-5-[(1S)-1-hydroxy-2-iodoethyl]phenyl}propanoate (0.550 g, 1.43 mmol) in ethanol (2.8 mL) was added [2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amine (0.273 g, 1.44 mmol) and K2CO3 (0.218 g, 1.58 mmol). The reaction was heated at 90° C. for 17 h. Upon cooling, the reaction was filtered and concentrated. Column chromatography (0-12% CH3OH:CH2Cl2) provided 0.315 g (49%) of the title compound: MS (ESI) 446.0 (M+H).

Workup

  1. temperatureUpon cooling
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ad3c8f8852f049b9864c4c03f10171ec
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

Loading…