4-[(4-{3-[(S)-5-Benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole → 4-[(4-(3-[(S)-5-Amino-1-(carbamoyl)pentylamino]propoxy)-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1869005Notes

Reaction equation

HRID 1869005 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2[C:33]([O:40][C@@H:41]3[O:49][C@H:48]([CH2:50][OH:51])[C@@H:46]([OH:47])[C@H:44]([OH:45])[C@H:42]3[OH:43])=[N:34][NH:35][C:36]=2[CH:37]([CH3:39])[CH3:38])=[C:27]([CH3:52])[CH:26]=1)[C:17](=[O:19])[NH2:18])=O)C1C=CC=CC=1>CO.[C].[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2[C:33]([O:40][C@@H:41]3[O:49][C@H:48]([CH2:50][OH:51])[C@@H:46]([OH:47])[C@H:44]([OH:45])[C@H:42]3[OH:43])=[N:34][NH:35][C:36]=2[CH:37]([CH3:39])[CH3:38])=[C:27]([CH3:52])[CH:26]=1)[C:17](=[O:19])[NH2:18]

Participants

4

Reactant 1

HCID 689410364-[(4-{3-[(S)-5-Benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Product 1

HCID 104160554-[(4-(3-[(S)-5-Amino-1-(carbamoyl)pentylamino]propoxy)-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazoleYield 93.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[(4-{3-[(S)-5-benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)-methyl]-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole (0.17 g) in methanol (4 mL) was added 10% palladium-carbon powder (30 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.13 g).

Workup

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

Sources & evidence

ORD record
ord-e8d858f372a243b1b35b9cef75f47297
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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