HCID 68942888, compound → HCID 68946870, compound

HRID 1869017Notes

Reaction equation

HRID 1869017 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41](CC3C=CC=CC=3)[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])=[CH:33][C:32]=2[CH3:54])=[C:28]([CH:55]([CH3:57])[CH3:56])[NH:27][N:26]=1)(=[O:3])[CH3:2]>CO.[C].[Pd]>[C:44]([CH2:43][CH2:42][NH:41][CH2:40][CH2:39][CH2:38][O: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][O:20][C:21](=[O:23])[CH3:22])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]3[O:4][C:1](=[O:3])[CH3:2])=[N:26][NH:27][C:28]=2[CH:55]([CH3:56])[CH3:57])=[C:32]([CH3:54])[CH:33]=1)(=[O:46])[NH2:45]

Participants

4

Reactant 1

HCID 68942888HCID 68942888, compound

Product 1

HCID 68946870HCID 68946870, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-[(4-{3-[N-benzyl-N-(2-carbamoylethyl)-amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole (75 mg) in methanol (3 mL) was added 10% palladium-carbon powder (20 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2.5 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give 4-[(4-{3-[2-(carbamoyl)ethylamino]propoxy}-2-methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazole (66 mg). This material was dissolved in methanol (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.03 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added acetic acid (0.04 mL), and the resulting mixture was concentrated under reduced pressure. The residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (43 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-932cc8892cbb49c4a623eb848207bc70
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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