Hydrochloric Acid → {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid

HRID 1795296Notes

Reaction equation

HRID 1795296 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][N:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:7]1=[O:28])C.O.[OH-].[Li+].Cl>O.CO>[C:24]([O:23][C:21]([N:16]([CH2:17][CH:18]1[CH2:19][CH2:20]1)[CH2:15][CH2:14][CH2:13][NH:12][C:8]1[C:7](=[O:28])[N:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:11]=[CH:10][N:9]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21023630{3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester

Product 1

HCID 22185113{3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester (250 mg, 0.61 mmol) and lithium hydroxide monohydrate (33 mg, 0.79 mmol) in water (0.72 ml) and methanol (3.6 ml) was stirred at room temperature for 2 h. hydrochloric acid solution (1N, 0.79 ml) was added and the reaction mixture was stirred at room temperature for 10 min. Concentration from methanol gave {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid; 1H NMR (CD3OD, 400 MHz) δ 6.78 (d, 1H, J=4.8 Hz), 6.69 (d, 1H, J=4.9 Hz), 4.61 (s, 2H), 3.32 (m, 4H), 3.12 (d, 2H, J=6.8 Hz), 1.89 (m, 2H), 1.45 (s, 9H), 1.00 (m, 1H), 0.48 (m, 2H), 0.22 (m, 2H).

Workup

  1. additionwas added
  2. concentrationConcentration from methanol

Sources & evidence

ORD record
ord-64e50937dd4741e08d1c6f28620cd315
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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