Lithium Hydroxide → HCID 178512497, compound

HRID 490936Notes

Reaction equation

HRID 490936 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[NH:16])=[CH:10][CH:9]=1)[CH2:6][SH:7])C.[Li+].[OH-].FC(F)(F)C(O)=O>O.C(O)C.O1CCCC1>[NH:14]([C:11]1[CH:10]=[CH:9][C:8]([CH:5]([CH2:6][SH:7])[C:4]([OH:18])=[O:3])=[CH:13][CH:12]=1)[C:15]([NH2:17])=[NH:16]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472286HCID 178472286, compound

Product 1

HCID 178512497HCID 178512497, compound

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of 2-(4guanidinophenyl)-3-mercaptopropanoic acid ethyl ester (60 mg) in 1:1:1 water/ethanol/tetrahydrofuran at 0° C. was added LiOH (130 mg). The reaction was stirred for 18 hours, acidified to pH 2 with trifluoroacetic acid and purified by preparative HPLC to afford 2-(4-guanidinophenyl)-3-mercaptopropanoic acid, as a trifluoroacetic acid salt, (15 mg); NMR (D2O) 2.75-2.83 (dd,1), 2.98-3.05 (dd,1), 3.75-3.80 (dd,1), 7.19 (d,2), 7.32 (d,2) ppm.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-00f5c9a85a004406bc70f758bd6ff691
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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