Glycine methyl ester hydrochloride → HCID 66608325, compound

HRID 563476Notes

Reaction equation

HRID 563476 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C([O-])(=O)C.[Na+].[CH:13]([C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[C:27]([CH2:33][C:34]([OH:36])=[O:35])[CH:26]=1)=O.C([BH3-])#N.[Na+]>CO.C(Cl)Cl.O>[CH3:32][O:31][C:30]1[C:25]([C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:15]=2[CH2:13][NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[CH:26][C:27]([CH2:33][C:34]([OH:36])=[O:35])=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 122755Glycine methyl ester hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86651102(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Product 1

HCID 66608325HCID 66608325, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Glycine methyl ester hydrochloride (0.057 g, 0.44 mmol) and sodium acetate (0.038 g, 0.44 mmol) were combined in a flask. (2′-Formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid (0.099 g, 0.29 mmol) in MeOH (3 mL) was added, followed by sodium cyanoborohydride (0.029 g, 0.44 mmol), and the reaction was stirred at room temperature for 3.5 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with CH2Cl2 and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f894fb12b4584545b4cfab21d6801a44
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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