Hydrochloric Acid → HCID 59519976, compound

HRID 1161950Notes

Reaction equation

HRID 1161950 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])[C:7](=[O:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([OH:14])=[O:13])[C:7](=[O:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68669637HCID 68669637, compound

Product 1

HCID 59519976HCID 59519976, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-butyl-2,3-dioxopiperazin-1-yl)-3-phenylpropanoate from Step A (130 mg, 0.39 mmol) in 10 mL THF and 3.9 mL water was added lithium hydroxide monohydrate (50 mg, 1.2 mmol). The reaction was stirred at rt for 2 h and HCl (1M, 1.2 mL) was added. Solvent evaporation gave 2-(4-butyl-2,3-dioxopiperazin-1-yl)-3-phenylpropanoic acid. 1H NMR (CD3OD) δ 7.26 (m, 5H), 5.18 (X of ABX, 1H, J=11.6 Hz, J=5 Hz), 3.55-3.17 (m, 8H), 1.50 (m, 2H), 1.27 (m, 2H), 0.92 (t, 3H, J=7.3 Hz).

Workup

  1. customSolvent evaporation

Sources & evidence

ORD record
ord-1df80913394b4f339cdf7a253d04b83e
Source dataset
uspto-grants-2010_10
Patent number
US07820674B2

Reaction notes

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