Hydrochloric Acid → HCID 178467028, compound

HRID 1266708Notes

Reaction equation

HRID 1266708 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[CH:20]=[C:19]([O:26][CH2:27][CH3:28])[C:18]=1[F:29])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[NH:16])[NH:14][OH:15])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1>[CH2:27]([O:26][C:19]1[C:18]([F:29])=[C:17]([CH:5]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13](=[NH:16])[NH:14][OH:15])=[CH:11][CH:12]=2)[C:4]([OH:30])=[O:3])[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[CH:20]=1)[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178472666HCID 178472666, compound

Product 1

HCID 178467028HCID 178467028, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (RS)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid ethyl ester (44 mg) described in example 2.5 was dissolved in THF (0.5 ml). IM NaOH (0.21 ml) was added and the mixture was stirred for 2 h at room temperature. The mixture was neutralized with 1 M HCl, concentrated and purified by column chromatography to give 23 mg of (RS)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid as a colorless solid. MS: 392 ([M+H]+) This compound was separated into the enantiomers by preparative HPLC on a chiral stationary phase (Chiralpak AD) using heptane/isopropanol/trifluoroacetic acid (60:40:0.2) as a mobile phase to give, after neutralisation, (R)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid and (S)-(3,5-diethoxy-2-fluoro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid.

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-09f60da8df6749bd90deb70bc8aa3540
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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