Lithium Hydroxide → 3-[[4-[[4-(Aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioic acid

HRID 1941549Notes

Reaction equation

HRID 1941549 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH2:18][C:19]([O:21]CC)=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH-].[Li+].C(O)(C(F)(F)F)=O>O.C(#N)C>[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 70062228Diethyl3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioate

Product 1

HCID 700611703-[[4-[[4-(Aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioic acidYield 57.4%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Diethyl 3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioate (700 mg) prepared in Example 19, Step 2 was added to water/acetonitrile (20 ml) followed by lithium hydroxide (150 mg) at 25° C. The mixture was stirred for 30 min. The course of the reaction was monitored by RPHPLC. After satisfactory product was formed the reaction was neutralized with TFA and purified by reverse phase chromatography (0.05% TFA water/acetonitrile) to result in 350 mg of a white solid: H NMR (d6 -DMSO) δ1.55 (m, 1H), 1.7 (m, 1H), 2.3 (m, 2H), 2.57 (m, 2H), 2.67 (m, 2H), 4.03 (m, 1H), 7.79 (s, 4H), 7.99 (d, 1H, J=8 Hz), 8.86 (bs, 2H), 9.17 (bs, 2H), 10.2 (s, 1H); MS (FAB) m/z 379.2 (MH+).

Workup

  1. customAfter satisfactory product was formed the reaction
  2. custompurified by reverse phase chromatography (0.05% TFA water/acetonitrile)

Sources & evidence

ORD record
ord-84146c44fa174e97b39eabb7c92e2fea
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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