3-Hydroxypropionic acid → Tert-butyl 4-(3-hydroxypropanoyl)piperazine-1-carboxylate

HRID 550794Notes

Reaction equation

HRID 550794 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:14][CH2:15][CH2:16][C:17](O)=[O:18].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15](=[O:14])[CH2:16][CH2:17][OH:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 681523-Hydroxypropionic acidHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67195617Tert-butyl 4-(3-hydroxypropanoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-tert-butoxycarbonylpiperazine, 3-hydroxypropionic acid, 1-hydroxybenzotriazole (HOBt), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI), and DMF was stirred at ambient temperature for 24 hours to yield 3-(4-tert-butoxycarbonylpiperazin-1-yl)-3-oxopropan-1-ol, which was stirred together with 4M HCl-dioxane solution and MeOH at ambient temperature for 16 hours to yield 3-oxo-3-piperazin-1-ylpropan-1-ol hydrochloride.

Sources & evidence

ORD record
ord-0f294de99ab747f8ba80a6d42380913b
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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