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Lithium Hydroxide → beta-[[2(R)-[[[[4(aminoiminomethyl)phenyl]amino]carbonyl]amino]methyl-propanoyl]-amino]1,3-benzodioxole-5-propanoic acid

HRID 55382
Notes
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Reaction equation

HRID 55382 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][CH2:14][C@@H:15]([CH3:35])[C:16]([NH:18][CH:19]([C:26]2[CH:34]=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[CH2:20][C:21]([O:23]CC)=[O:22])=[O:17])=[O:12])=[CH:6][CH:5]=1.[OH-].[Li+]>CO.O>[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][CH2:14][C@@H:15]([CH3:35])[C:16]([NH:18][CH:19]([C:26]2[CH:34]=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[CH2:20][C:21]([OH:23])=[O:22])=[O:17])=[O:12])=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86747887ethyl beta-[[2(R)-[[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]-amino]methylpropanoyl]amino]-1,3-benzodioxole-5-propanoate

Product 1

HCID 86747886beta-[[2(R)-[[[[4(aminoiminomethyl)phenyl]amino]carbonyl]amino]methyl-propanoyl]-amino]1,3-benzodioxole-5-propanoic acidYield 71.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)
Solvent

Procedure

A portion of ethyl β-[[2(R)-[[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]-amino]methylpropanoyl]amino]-1,3-benzodioxole-5-propanoate (0.18 g; 0.37 mmoles)) was then treated with 1N lithium hydroxide in methanol/water (1:1; 10 ml) for 15 min. The solvents were evaporated under reduced pressure and the residue was dissolved in water/acetonitrile. The crude product was purified by HPLC (C-18 DeltaPak column) using a gradient of acetonitrile/water/trifluoroacetic acid. Both diastereomers were separated and the desired fractions were lyophilized to give 121 mg of white solid (71% combined yield). FAB-MS: MH+ =456.3 (isomer 1) and 456.2 (isomer 2).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water/acetonitrile
  3. customThe crude product was purified by HPLC (C-18 DeltaPak column)
  4. customBoth diastereomers were separated

Sources & evidence

ORD record
ord-ec1f91f9d22b4f8780dfa3a44b4287d7
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05624956

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes