Lithium hydroxide, monohydrate → HCID 178514398, compound

HRID 2270871Notes

Reaction equation

HRID 2270871 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:25]([O:27]C)=[O:26])[NH:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:13])=[CH:8][C:7]=1[Cl:23].[NH2:29][N:30]=[CH:31]S(O)(=O)=O.O.[OH-].[Li+]>CO.C(N(CC)CC)C>[Cl:23][C:7]1[CH:8]=[C:9]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:13])[CH:10]=[CH:11][C:6]=1[C:5]([NH:4][C@H:3]([C:25]([OH:27])=[O:26])[CH2:2][NH:1][CH:31]=[N:30][NH2:29])=[O:24]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 3013981Aminoiminomethane-sulphonic acidHCID 599772583-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester

Product 1

HCID 178514398HCID 178514398, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester (Example 72; 50 mg, 0.123 mmol) in methanol (2 mL) were added triethylamine (3 drops) and aminoiminomethanesulfonic acid (prepared according to Kim, K. et al. Tetrahedron Lett. 1988, 29, 3183-3186; 37 mg, 0.30 mmol). The reaction was stirred at room temperature overnight, and then the solvent was evaporated. The residue was suspended in tetrahydrofuran/methanol/water (3:1:1; 2 mL) and lithium hydroxide monohydrate (20 mg, 0.48 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, then the solvent was evaporated and the residue was purified by reverse phase HPLC to give N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-(aminoiminomethyl)amino-L-alanine (17 mg, 33%) as a white powder.

Workup

  1. customthe solvent was evaporated
  2. stirringThe reaction mixture was stirred at room temperature for 1 h
  3. customthe solvent was evaporated
  4. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-288180331e3b4dc9ba36b501df60e89a
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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