Hydrochloric Acid → HCID 178513192, compound

HRID 23997Notes

Reaction equation

HRID 23997 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH:26][C:27]([NH2:29])=[NH:28])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>CO.O>[NH:26]([O:25][CH2:24][CH2:23][O:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[N:13]([CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:5][C:4]([OH:30])=[O:3])[CH:14]=[CH:15]2)[C:27]([NH2:29])=[NH:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178470875HCID 178470875, compound

Product 1

HCID 178513192HCID 178513192, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

3-(5-{2-[guanidino-oxy]-ethoxy}-indol-1-yl)-3-phenyl-propionic acid ethyl ester (0.30 gg, 0.71 mmol) was dissolved in 70% methanol/water (4 mL) and lithium hydroxide monohydratate (0.70 g, 4.67 mmol) was added. The reaction was stirred for 16 h at room temperature under an argon atmosphere. The solution was neutralized with 1.0 N HCl (4.67 mL) and the solvent was evaporated under vacuum. The crude mixture was purified via column chromatography with silica gel, eluting with 10% methanol/dichloromethane to afford the title compound (80% yield). 1H NMR (CD3OD-d4) δ 7.34 (d, 1H, J=3.2 Hz), 7.06-7.15 (m, 6H), 6.97 (d, 1H, J=2.3 Hz), 6.65 (dd, 1H, J=2.5, 9.0 Hz), 6.31 (d, 1H, J=3.2 Hz), 5.93 (t, 1H, J=7.0 Hz), 4.01 (m, 4H), 3.07 (m, 2H).

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe crude mixture was purified via column chromatography with silica gel
  3. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-9c5bbf11eea043a493242e6fed2ed7f3
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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