Acetic Acid → 3-(4-{2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propylamino}-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 860687Notes

Reaction equation

HRID 860687 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[CH3:13].[CH:15]([C:18]1[N:19]=[C:20]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[S:21][C:22]=1[CH:23]([CH3:26])[CH:24]=O)([CH3:17])[CH3:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:26][CH:23]([C:22]2[S:21][C:20]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=3)=[N:19][C:18]=2[CH:15]([CH3:17])[CH3:16])[CH3:24])=[CH:8][C:7]=1[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoateHCID 587657272-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde

Product 1

HCID 695895783-(4-{2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propylamino}-2-methyl-phenyl)-propionic Acid Methyl EsterYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-Amino-2-methyl-phenyl)-propionic acid methyl ester (0.7.0 mmol) and 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde (0.71 mmol) in anhydrous CH2Cl2 (5 mL) is added 4 Å molecular sieves followed by acetic acid (50 μL, 0.87 mmol). The mixture is stirred at RT for 2 h. Sodium triacetoxyborohydride (0.22 g, 1.04 mmol) is added, and the mixture is stirred at RT for 12 h. The reaction is quenched with saturated NaHCO3. The organics are separated and washed with saturated NaHCO3 and brine, and dried with MgSO4. The crude material is purified by flash chromatography to yield the title compound (0.21 g, 68%).

Workup

  1. stirringthe mixture is stirred at RT for 12 h
  2. customThe reaction is quenched with saturated NaHCO3
  3. customThe organics are separated
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried with MgSO4
  6. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-367f17995b35451986ced5a4b80eb6fa
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

Loading…