DL-beta-Phenylalanine → HCID 78164777, compound

HRID 1481098Notes

Reaction equation

HRID 1481098 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][CH:26]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+]>CN(C=O)C>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][CH:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][C:28]([OH:30])=[O:29])=[O:4])[N:6]=1)#[N:24]

Participants

5

Reactant 3

HCID 69189DL-beta-PhenylalanineHCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 78164777HCID 78164777, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol) and 3-amino-3-phenyl-propionic acid (257 mg, 1.56 mmol) (Sigma-Aldrich) in 3 mL of DMF was added NaOMe solid (67 mg, 1.25 mmol). The resultant mixture was heated in a 150° C. oil bath for 3 h. After cooled, insoluble was filtered off. Filtrate was diluted with water (100 mL). This suspension mixture was brought to clear by adding 1 N NaOH (pH=ca. 10). It was then acidified by 1 N HCl to pH=3-4 and extracted with EtOAc. Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound 103 mg (0.227 mmol) in 73% yield. LC-MS ESI−: 451.95 (M−1)−.

Workup

  1. temperatureAfter cooled
  2. filtrationinsoluble was filtered off
  3. additionFiltrate was diluted with water (100 mL)
  4. additionby adding 1 N NaOH (pH=ca. 10)
  5. extractionextracted with EtOAc
  6. washOrganic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-81b17f498e1e4801b16c1305825b9206
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…