Lithium Hydroxide → HCID 65550994, compound

HRID 593206Notes

Reaction equation

HRID 593206 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:18])[CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[N:8][CH:9]=1>O1CCCC1.O.[Na]>[Br:3][C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89437205HCID 89437205, compound

Product 1

HCID 65550994HCID 65550994, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 5360545SodiumSolvent

Procedure

Lithium hydroxide (0.058 g, 1.0 eq.) was added at room temperature to a solution of methyl 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoate (Example II, 0.400 g, 1.0 eq.) in a mixture of tetrahydrofuran (15 mL) and water (5 mL). The reaction mixture was stirred at room temperature. The residue was diluted with a saturated solution of sodium hydrogenocarbonate and washed with ethyl acetate. The aqueous phase was acidified by addition of aqueous hydrochloric acid (concentrated) and extracted twice with ethyl acetate. The combined organic layer was dried on magnesium sulfate and concentrated under vacuum to give the desired compound 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoic acid A3 (0.343 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.18 (bs, 1H), 11.02 (s, 1H), 9.12 (s, 1H), 8.60 (s, 1H), 2.67 (t, 2H), 2.55 (m, 2H) ppm. LC-MS (Method A): RT 1.08, 274 (M−H+)

Workup

  1. washwashed with ethyl acetate
  2. additionThe aqueous phase was acidified by addition of aqueous hydrochloric acid (concentrated)
  3. extractionextracted twice with ethyl acetate
  4. customThe combined organic layer was dried on magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7998f00634a740b3bba183cec60d77c6
Source dataset
uspto-grants-2016_01
Patent number
US09241489B2

Reaction notes

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