Hydrochloric Acid → {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-6-chloro-2-oxo-2H-pyrazin-1-yl}-acetic acid

HRID 1795298Notes

Reaction equation

HRID 1795298 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:7]1=[O:29])C.O.[OH-].[Li+].Cl>O.CO>[C:25]([O:24][C:22]([N:17]([CH2:18][CH:19]1[CH2:20][CH2:21]1)[CH2:16][CH2:15][CH2:14][NH:13][C:8]1[C:7](=[O:29])[N:6]([CH2:5][C:4]([OH:30])=[O:3])[C:11]([Cl:12])=[CH:10][N:9]=1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21023631{3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-6-chloro-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester

Product 1

HCID 22185165{3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-6-chloro-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]-6-chloro-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester (0.22 g, 0.50 mmol) and lithium hydroxide monohydrate (27 mg, 0.65 mmol) in water (0.65 ml) and methanol (3 ml) was stirred at room temperature for 1.5 h. hydrochloric acid solution (1N, 0.65 ml) was added and the reaction mixture was stirred at room temperature for 5 min. Concentration from methanol gave {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-6-chloro-2-oxo-2H-pyrazin-1-yl}-acetic acid; 1H NMR (CD3OD, 400 MHz) δ 6.90 (s, 1H), 4.90 (s, 2H), 3.34 (m, 4H), 3.11 (d, 2H, J=6.8 Hz), 1.88 (m, 2H), 1.45 (s, 9H), 0.99 (m, 1H), 0.49 (m, 2H), 0.22 (m, 2H).

Workup

  1. additionwas added
  2. concentrationConcentration from methanol

Sources & evidence

ORD record
ord-e55785e5cddb4f18a973806cf23bd54d
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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