Lithium hydroxide, monohydrate → HCID 10805749, compound

HRID 990707Notes

Reaction equation

HRID 990707 reaction equation
C([O:8][C:9](=[O:29])[CH2:10][N:11]1[C:16]([CH3:17])=[C:15]([Cl:18])[N:14]=[C:13]([NH:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]1=[O:28])C1C=CC=CC=1.C1COCC1.CO.O[Li].O>O>[Cl:18][C:15]1[N:14]=[C:13]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:12](=[O:28])[N:11]([CH2:10][C:9]([OH:29])=[O:8])[C:16]=1[CH3:17]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 10692987HCID 10692987, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 10805749HCID 10805749, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Water (1 ml) was added to a stirred solution of (5-chloro-6-methyl-2-oxo-3-phenethylamino-2H-pyrazin-1-yl)acetic acid benzyl ester (436 mg) in 1:1 THF/MeOH (6 ml) and LiOH.H2O was added to the resulting mixture. After 2 h, the reaction mixture was diluted with water and washed with EtOAc. The aqueous layer was acidified with 10% KHSO4 solution to give a cloudy mixture that was extracted with methylene chloride. The organic layer was dried (Na2SO4) and evaporated in vacuo to give 1-4 as a crystalline solid. 1H NMR (DMSO-d6) δ2.19 (s, 3 H, Me), 2.84 (t, J=7.0 Hz, 2 H, PhCH2), 3.45 (q, J=7.0 Hz, 2 H, CH2NH), 4.70 (s, 2 H, CH2CO2), 7.18-7.31 (m, 5 H, Ph), 7.46 (br s, 1H, NH).

Workup

  1. additionwas added to the resulting mixture
  2. washwashed with EtOAc
  3. customto give a cloudy mixture that
  4. extractionwas extracted with methylene chloride
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b321054e1234c3aaa7b4e4a27e9476c
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

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