Diethylamine → (2S)-4-(5-chloro-2-fluorophenyl)-2-(3-hydroxyphenyl)-1-(2-methylalanyl)-2,5-dihydro-1H-pyrrole

HRID 2054752Notes

Reaction equation

HRID 2054752 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2[CH2:12][N:11]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[NH2:15])[CH:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)[CH:9]=2)[CH:7]=1.C(NCC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2[CH2:12][N:11]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[NH2:15])[C@H:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 596566024-(5-chloro-2-fluorophenyl)-2-(3-hydroxyphenyl)-1-(2-methylalanyl)-2,5-dihydro-1H-pyrrole

Product 1

HCID 58641415(2S)-4-(5-chloro-2-fluorophenyl)-2-(3-hydroxyphenyl)-1-(2-methylalanyl)-2,5-dihydro-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Resolution of enantiomers of racemic 4-(5-chloro-2-fluorophenyl)-2-(3-hydroxyphenyl)-1-(2-methylalanyl)-2,5-dihydro-1H-pyrrole (3-4) by chiral normal-phase BPLC (Chiralcel OD column: 0.1% diethylamine in 10% ethanol in hexanes initially, grading to 30% ethanol in hexanes) provided (2S)-4-(5-chloro-2-fluorophenyl)-2(3-hydoxyphenyl)-1-(2-methylalanyl)-2,5-dihydro-1H-pyrrole (3-5) as the first eluting, minus (−) enantiomer.

Sources & evidence

ORD record
ord-b2d13acffcce46dbb3de959c6c0e2aea
Source dataset
uspto-grants-2008_02
Patent number
US07329762B2

Reaction notes

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