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

HRID 1941555Notes

Reaction equation

HRID 1941555 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH:5]([NH:10][C:11](=[O:26])[CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]=[N:24][NH2:25])=[CH:19][CH:18]=1)=[O:15])[CH:6]([O:8][CH3:9])[CH3:7].[OH-].[Li+].C(O)(C(F)(F)F)=O>O.C(#N)C>[NH2:25][N:24]=[CH:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[CH2:13][CH2:12][C:11]([NH:10][CH:5]([CH:6]([O:8][CH3:9])[CH3:7])[CH2:4][C:3]([OH:27])=[O:2])=[O:26])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 70062635Methyl-3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-methoxypentanoate

Product 1

HCID 700621253-[[4-[[4-(Aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-methoxypentanoic acidYield 93.5%

Reagents, catalysts & solvents 1

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

Procedure

Methyl-3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-methoxypentanoate prepared in Example 25, 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 (water/acetonitrile) to result in 450 mg of a white solid: 1H NMR (d6 -DMSO) δ1.74 (m, 2H), 2.4 (m, 4H), 2.6 (m, 2H), 3.16 (s, 3H), 3.33 (m, 2H), 4.12 (m, 1H), 7.78 (s, 4H), 7.81 (d, 1H, J=8.5 Hz), 9.02 (bs, 2H), 9.15 (bs, 2H), 10.40 (s, 1H); MS (FAB) m/z 365.4 (MH+).

Workup

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

Sources & evidence

ORD record
ord-20dd91843c5441d4be75d7a86606e817
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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