Hydrochloric Acid → HCID 66894654, compound

HRID 19133Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[C:16]=2[F:23])=[CH:11][C:10]1=[O:24])[CH2:5][CH:6]([CH3:8])[CH3:7].B(Br)(Br)Br.Cl>ClCCl>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:16]=2[F:23])=[CH:11][C:10]1=[O:24])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-2-[4-(2-fluoro-3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid methyl ester (1.35 g, 3.83 mmol) in dichloromethane (20 mL) was added a boron tribromide in dichloromethane solution (1 M, 11.50 mL, 11.50 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 2 h and then poured into ice water containing hydrochloric acid (2N, 30 mL). The organic phase was separated, washed with water and brine. The solvents were removed by evaporation and the residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 30% to 100% (9:1 dichloromethane:methanol)/hexanes) which afforded (S)-2-[4-(2-fluoro-3-hydroxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid methyl ester (1.05 g, 81%) as a brown oil.

Workup

customThe organic phase was separated
washwashed with water and brine
customThe solvents were removed by evaporation
customthe residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 30% to 100% (9:1 dichloromethane:methanol)/hexanes) which

Sources & evidence

ORD record: ord-8b1631fc83374c61a7819317092e4056
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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