Ethanol → HCID 58641201, compound

HRID 1394961Notes

Reaction equation

HRID 1394961 reaction equation
[CH:1]1([C@H:4]([NH2:26])[C:5]([N:7]2[CH2:11][C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])=[CH:9][C@H:8]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:6])[CH2:3][CH2:2]1.[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29].C(O)C>O1CCOCC1>[CH:1]1([C@H:4]([NH:26][CH2:29][CH2:28][C:27]([O:31][CH3:32])=[O:30])[C:5]([N:7]2[CH2:11][C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])=[CH:9][C@H:8]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 7294Methyl AcrylateHCID 6102824HCID 6102824, compound

Product 1

HCID 58641201HCID 58641201, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of {(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}amine (16-7, 100 mg, 0.282 mmol, 1 equiv) and methyl acrylate (0.076 mL, 0.85 mmol, 3.0 equiv) in a 1:1 mixture of ethanol and dioxane (10 mL) was heated at 85° C. for 20 h. The reaction mixture was concentrated and the residue was purified by flash column chromatography (100% EtOAc) to provide methyl N-{(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}-β-alaninate (41-1) as a colorless oil that solidified to a white solid over time. LRMS m/z (M+H) 441.4 found, 441.2 required.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-cb29f517e31c459eaf8e45e6152deabc
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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