1-(2-Hydroxyethyl)piperazine → HCID 9961304, compound

HRID 1442395Notes

Reaction equation

HRID 1442395 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][C:40](=[O:48])[NH:41][C:42]([C:45](O)=[O:46])([CH3:44])[CH3:43])=[CH:33][CH:32]=2)=[C:28]([CH:49]([CH3:51])[CH3:50])[NH:27][N:26]=1)(=O)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH:74][CH2:75][CH2:76][N:77]1[CH2:82][CH2:81][NH:80][CH2:79][CH2:78]1.[OH-].[Na+]>CN(C)C=O.O.C(O)(=O)C>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][CH2:39][C:40](=[O:48])[NH:41][C:42]([C:45]([N:80]4[CH2:81][CH2:82][N:77]([CH2:76][CH2:75][OH:74])[CH2:78][CH2:79]4)=[O:46])([CH3:44])[CH3:43])=[CH:35][CH:36]=3)=[C:28]([CH:49]([CH3:51])[CH3:50])[NH:27][N:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

9

Reactant 5

HCID 76771-(2-Hydroxyethyl)piperazineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68535853HCID 68535853, compound

Product 1

HCID 9961304HCID 9961304, compoundYield 14.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-galacto-pyranosyloxy)-4-[(4-{3-[1-carboxy-1-(methyl)ethyl-carbamoyl]propyl}phenyl)methyl]-5-isopropyl-1H-pyrazole (30 mg) in N,N-dimethylformamide (0.5 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12 mg), 1-hydroxybenzotriazole (9 mg) and 1-(2-hydroxyethyl)piperazine (54 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 5 mol/L aqueous sodium hydroxide solution (0.25 mL), and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added acetic acid (0.1 mL), and the mixture was diluted with water (1 mL). The insoluble material was removed by filtration, and the filtrate was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μL, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/acetonitrile=90/10-10/60) to give the title compound (4 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. customThe insoluble material was removed by filtration
  3. customthe filtrate was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μL, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/acetonitrile=90/10-10/60)

Sources & evidence

ORD record
ord-57a9bde45b734bb2b4739db814d965b4
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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