Hydrochloric Acid → (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochloride

HRID 1396999Notes

Reaction equation

HRID 1396999 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:16](=[O:31])[N:17]2[C@H:21]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[O:23])[CH2:20][CH:19]=[N:18]2)[CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:32].O1CCOCC1>>[ClH:32].[CH:1]1([CH2:6][C@@H:7]([C:16](=[O:31])[N:17]2[C@H:21]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[O:23])[CH2:20][CH:19]=[N:18]2)[CH2:8][C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 867064101,1-Dimethylethyl (3R)-3-(cyclopentyl methyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoate

Product 1

HCID 131732111(3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochlorideYield 100%

Procedure

To a 500 ml round bottom flask was added 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoate (29.1 g, 58.4 mmol) and 4 M HCl in 1,4-dioxane (240 mL, 960 mmol). The mixture was stirred at room temperature and monitored by LCMS. After 90 min, no starting material remained. The mixture was concentrated to dryness and co-evaporated with dioxane (2×15 mL) to afford the crude (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochloride (34.0 g, 58.5 mmol, 100% yield) as a light brown foamy solid that was used directly for the next step. LCMS: [M+H]+: 373.2.

Workup

  1. concentrationThe mixture was concentrated to dryness and co-evaporated with dioxane (2×15 mL)

Sources & evidence

ORD record
ord-0b8f3a988a794854986956492e6941b8
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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