Lithium Hydroxide → HCID 86758118, compound

HRID 2184918Notes

Reaction equation

HRID 2184918 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)=[C:11](/[F:20])\[C:12]([NH:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[NH:3])[NH2:2].[OH-].[Li+]>CO>[C:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:36])(=[O:37])[NH2:35])=[CH:24][CH:23]=2)=[C:11](/[F:20])\[C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[NH:2])[NH2:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86758119HCID 86758119, compound

Product 1

HCID 86758118HCID 86758118, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-{(2E)-3-(3-amidinophenyl)-2-fluoro-N-[4-(2-sulfamoylphenyl)phenyl]but-2-enoylamino}acetate (100 mg, 0.19 mmol) in 5 ml methanol was added a 0.5N lithium hydroxide solution (1 ml, 0.5 mmol). The reaction was stirred at room temperature for 4 hours then concentrated and purified on a 2×25 cm Vydac C18 HPLC column to give 2-{(2E)-3-(3-amidinophenyl)-2-fluoro-N-[4-(2-sulfamoylphenyl)phenyl]but-2-enoylamino}acetic acid (70 mg, 71%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 511.1.

Workup

  1. concentrationthen concentrated
  2. custompurified on a 2×25 cm Vydac C18 HPLC column

Sources & evidence

ORD record
ord-6ec30346176545878676c445e862da41
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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