Phenylpyruvic acid → HCID 11617017, compound

HRID 2380763Notes

Reaction equation

HRID 2380763 reaction equation
O=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:13]1([C:19]2[N:20]=[C:21](NC)[S:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH3-][C:27]#[N:28].[Na+]>CO>[C:7]1([CH2:6][CH:2]([NH:28][CH2:27][C:21]2[S:22][CH:23]=[C:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:20]=2)[C:3]([OH:5])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 824443N-methyl-4-phenyl-1,3-thiazol-2-amineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 11617017HCID 11617017, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-Oxo-3-phenyl-propionic acid (1.6 mmol, 264 mg) and (4-Phenyl-thiazol-2-yl)-methylamine (1.0 mmol, 190 mg) in MeOH (4 mL), is added NaBH3CN (2.0 mmol, 1N in THF). The pH was then adjusted at 6 with 1M HClaq. The mixture was stirred at room temperature for 3 days. The product was purified by HPLC to give the pure product (210 mg, 62%).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-accdf6f97f42477495e66d1febd6ca08
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

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