Ammonium Chloride → 4-({4-[(1E)-3-Carbamoylprop-1-enyl]phenyl}methyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 2223587Notes

Reaction equation

HRID 2223587 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](/[CH:37]=[CH:38]/[CH2:39][C:40](O)=[O:41])=[CH:33][CH:32]=2)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[Cl-].[NH4+].O[N:49]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[C:40]([CH2:39]/[CH:38]=[CH:37]/[C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:43]([CH3:44])[CH3:45])=[CH:32][CH:33]=1)(=[O:41])[NH2:49]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685375513-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole

Product 1

HCID 685360104-({4-[(1E)-3-Carbamoylprop-1-enyl]phenyl}methyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazoleYield 29.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole (32 mg) in N,N-dimethylformamide (1 mL) were added ammonium chloride (8 mg), 1-hydroxybenzotriazole (9 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15 mg) and triethylamine (21 mg), and the mixture was stirred at room temperature overnight. The insoluble material was removed by filtration, 5 mol/L aqueous sodium hydroxide solution (0.5 mL) was added to the filtrate, and the resulting mixture was stirred at room temperature for 1 hour. The insoluble material was removed by filtration, and the filtrate was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/acetonitrile=90/10-10/90) to give the title compound (7 mg).

Workup

  1. customThe insoluble material was removed by filtration, 5 mol/L aqueous sodium hydroxide solution (0.5 mL)
  2. additionwas added to the filtrate
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. customThe insoluble material was removed by filtration
  5. customthe filtrate was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/acetonitrile=90/10-10/90)

Sources & evidence

ORD record
ord-ec6a538d09a54449b16696cb8fe7d89c
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

Loading…