Lithium Hydroxide → HCID 70061729, compound

HRID 1941552Notes

Reaction equation

HRID 1941552 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH:18]([C:22]([O-:24])=[O:23])[C:19]([O-:21])=[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:25])[CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH:18]([C:19]([OH:21])=[O:20])[C:22]([OH:24])=[O:23])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 86751795HCID 86751795, compound

Product 1

HCID 70061729HCID 70061729, compoundYield 69.6%

Reagents, catalysts & solvents 1

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

Procedure

Dimethyl [[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]aminomethyl]propanedioate prepared in Example 23, Step 2 (500 mg) was added to water/acetonitrile (20 ml) followed by lithium hydroxide (100 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 (0.5% TFA water/acetonitrile) to result in 350 mg of a white solid: 1H NMR (d6 -DMSO) δ2.41 (m, 2H), 2.57 (m, 2H), 3.35 (m, 1H), 3.47 (m, 2H), 7.79 (s, 4H), 8.1 (t, 1H, J=6.1 Hz), 7.78 (s, 4H), 8.02 (m, 1H), 8.87 (bs, 2H), 9.15 (bs, 2H), 10.39 (s, 1H); MS (FAB) m/z 350 (MH+).

Workup

  1. customAfter satisfactory product was formed the reaction
  2. custompurified by reverse phase chromatography (0.5% TFA water/acetonitrile)

Sources & evidence

ORD record
ord-4a9b59acfdef45de8dcd5472ad03d718
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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