Lithium hydroxide, monohydrate → (S)-5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylic acid

HRID 596127Notes

Reaction equation

HRID 596127 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:29]([O:31]CC)=[O:30])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:27])[NH:15][C@@H:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([Br:26])[CH:20]=2)[CH2:17][OH:18])=[C:10]([F:28])[CH:9]=1.O[Li].O>CO.C1COCC1.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:29]([OH:31])=[O:30])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:27])[NH:15][C@@H:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([Br:26])[CH:20]=2)[CH2:17][OH:18])=[C:10]([F:28])[CH:9]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118054716(S)-ethyl 5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylate

Product 1

HCID 118046022(S)-5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-ethyl 5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylate (220 mg, 0.422 mmol) and LiOH.H2O (142 mg, 3.38 mmol) in MeOH (2 ml), THF (2 mL) and Water (2 mL) was stirred for 3 hours at RT. The mixture was concentrated, to the residue was added 2 ml of water, 3N HCl was then added under stirring until the final pH was about 4. The resultant mixture was then concentrated and further dried to afford the crude product was a light yellow solid. (208 mg, 0.422 mmol, 100% yield). LC-MS (m/z): 494.9 (MH+), 0.653 min.

Workup

  1. concentrationThe mixture was concentrated, to the residue
  2. additionwas added 2 ml of water, 3N HCl
  3. additionwas then added
  4. stirringunder stirring until the final pH was about 4
  5. concentrationThe resultant mixture was then concentrated
  6. customfurther dried

Sources & evidence

ORD record
ord-7d4376fcf5ab49c78030ea65935b08d7
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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