Lithium hydroxide, monohydrate → HCID 58305717, compound

HRID 2280314Notes

Reaction equation

HRID 2280314 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][C:18]=4[CH3:25])[C:15]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O.[OH-].[Li+]>C1COCC1.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][C:18]=4[CH3:25])[C:15]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58305611HCID 58305611, compound

Product 1

HCID 58305717HCID 58305717, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-(aminomethyl)-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (30C) (300 mg) in THF/H2O (v/v=1/1, 6 mL) was added lithium hydroxide monohydrate (50.4 mg, 2.10 mmol). The solution was stirred at room temperature overnight. THF was removed under reduced pressure and the resulting solution was acidified with 10% hydrochloric acid to pH=6.0. The resulting precipitate was isolated by centrifuge, rinsed with water, dried under reduced pressure and purified by prep-HPLC to afford 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-(aminomethyl)-2-methylphenyl)-1H-pyrrol-2-yl)propanoic acid (30D) (170 mg, 74%) as a yellow solid.

Workup

  1. customTHF was removed under reduced pressure
  2. customThe resulting precipitate was isolated by centrifuge
  3. washrinsed with water
  4. customdried under reduced pressure
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-aab62fa43137451b9f53dca5b84cd9e9
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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