Ethanol → HCID 11668171, compound

HRID 1162548Notes

Reaction equation

HRID 1162548 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:16]CC#N)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:29][C:28]([OH:26])=[O:30])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68648406HCID 68648406, compound

Product 1

HCID 11668171HCID 11668171, compound

Procedure

3-{[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionic acid was prepared following general procedure I using 3-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionitrile (368 mg, 1 mmol), 1 N NaOH (aq) solution (4 mL) and ethanol (2 mL). The mixture was refluxed for 15 h. Trituration in hexanes gave 3-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionic acid. LCMS m/z: 387 (M+1)+. The sodium salt was prepared following general procedure J using 3-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionic acid (93.8 mg, 0.243 mmol), 1 N NaOH (aq) solution (0.243 mL), THF (1 mL) and MeOH (1 mL). Trituration in hexanes gave sodium 3-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionate.

Workup

  1. custom3-{[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionic acid was prepared
  2. temperatureThe mixture was refluxed for 15 h

Sources & evidence

ORD record
ord-5558e7806b16477fba2e6fda0834bb2f
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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