Lithium hydroxide, monohydrate → (Phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic Acid

HRID 2252459Notes

Reaction equation

HRID 2252459 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH:12]([CH2:16][NH:17][C:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH2:29][CH2:30][CH2:31][NH:32][C:33]2[N:34]([C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:35]=[CH:36][N:37]=2)[N:24]=[CH:23]3)=[O:19])[C:13]([O-:15])=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1.O>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH:12]([CH2:16][NH:17][C:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH2:29][CH2:30][CH2:31][NH:32][C:33]2[N:34]([C:38]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:35]=[CH:36][N:37]=2)[N:24]=[CH:23]3)=[O:19])[C:13]([OH:15])=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131726744(phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoate

Product 1

HCID 20707264(Phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic AcidYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoate (1.55 g, 2.03 mmol) was dissolved in tetrahydrofuran (20 mL). Lithium hydroxide monohydrate (1.71 g, 40.6 mmol) was dissolved in water and added to the reaction. The reaction was stirred overnight under N2 for 18 h. The tetrahydrofuran was removed under high vacuum. The pH of the remaining aqueous layer was adjusted to 5 with 1N HCl. The aqueous layer was extracted with methylene chloride. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated to an oil under high vacuum. The oil was recrystallized from hexane:ethyl acetate to give 800.9 mgs (53%) of product. ESMS: Calcd. for C44H41N7O5, 747.32. Found, 748.3 [M+H]+1 Analytical HPLC, Method A, Rt=15.66 min, Purity=94%.

Workup

  1. additionadded to the reaction
  2. customThe tetrahydrofuran was removed under high vacuum
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil under high vacuum
  8. customThe oil was recrystallized from hexane

Sources & evidence

ORD record
ord-daacbba00215417aa59de2a474c5f15e
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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