Lithium Chloride → HCID 69252307, compound

HRID 902676Notes

Reaction equation

HRID 902676 reaction equation
C[O:2][C:3](=[O:39])[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:29]=2[Cl:38])[CH2:18][C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[CH:8]=1)([CH3:6])[CH3:5].[Li+].[Cl-]>CN(C=O)C>[ClH:38].[Cl:38][C:29]1[C:30]([C:34]([F:35])([F:36])[F:37])=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][N:17]([CH2:18][C@H:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:20])[CH2:16][CH2:15][CH2:14][O:13][C:9]1[CH:8]=[C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:39])=[O:2])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 69254399HCID 69254399, compound

Product 1

HCID 69252307HCID 69252307, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-propoxy}-phenyl)-2-methyl-propionic acid methyl ester (30 mg, 0.05 mmol) in DMF (9 ml) was treated with LiCl (20 mg, 0.46 mmol). The resulting reaction mixture was heated to reflux overnight and concentrated under vacuum. The crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give the title compound free amine as an oil (15 mg, 45%). MS m/e 548.2(M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M) to precipitate the amine salt. The suspension was filtered and dried to give the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-daa36ca614f2481c8225a5149f4c928e
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…