Glycine methyl ester → [2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic Acid Methyl Ester

HRID 902695Notes

Reaction equation

HRID 902695 reaction equation
[Cl:1][C:2]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH:17]=O)[CH:13]=[CH:14][CH:15]=1.[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH2:45].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH:45][CH2:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:33]=[CH:34][CH:35]=[C:36]([C:37]([F:38])([F:40])[F:39])[C:2]=2[Cl:1])[CH2:19][CH:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 69221Glycine methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 86598296(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde

Product 1

HCID 69251469[2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde (76 mg, 0.13 mmol) and glycine methyl ester (34 mg, 0.27 mmol) in 1,2-dichloroethane (15 ml) was stirred as room temperature for 10 minutes, and sodium triacetoxyborohydride (57 mg, 0.27 mmol) was added. Next two drops of glacial acetic acid was added. The reaction mixture was stirred at room temperature for 18 hour and then quenched with 0.01N aqueous HCl (15 ml) The biphasic mixture was separated and the aqueous layer was extracted with dichloromethane (3×). The organic layers were combined with the 1,2-dichloroethane solution and were washed with brine (1×), dried over sodium sulphate, filtered and concentrated in vacuo. Preparative HPLC (YMC 75×30 mm, 25 ml/min, 90-100% CH3CN) afforded title compound as an oil, 70 mg (81%).

Workup

  1. customquenched with 0.01N aqueous HCl (15 ml) The biphasic mixture
  2. customwas separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×)
  4. washwere washed with brine (1×)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c4b2760b61945e8b91a6fe7a7bcea6f
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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