Hydrochloric Acid → (3R)-3-(cyclopentylmethyl)-4-{5-[(dimethylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoic acid

HRID 1396980Notes

Reaction equation

HRID 1396980 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:16]([N:18]2[CH:22]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:21][CH:20]=[N:19]2)=[O:17])[CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([CH2:6][C@@H:7]([C:16]([N:18]2[CH:22]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:21][CH:20]=[N:19]2)=[O:17])[CH2:8][C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 682880781,1-dimethylethyl (3R)-3-(cyclopentyl methyl)-4-{5-[(dimethylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoate

Product 1

HCID 68287954(3R)-3-(cyclopentylmethyl)-4-{5-[(dimethylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-{5-[(dimethylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoate (315 mg, 0.83 mmol) in 1,4-dioxane (5.0 mL) was added 4.0 M hydrochloric acid in 1,4-dioxane (10.4 mL, 42 mmol) at room temperature. The reaction mixture was stirred for 4 hours. The solvent was then removed by reduced pressure to afford the crude product, (3R)-3-(cyclopentylmethyl)-4-{5-[(dimethylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoic acid (269 mg, 100% yield), which was used directly in the next step. MS: 324 ([M+H]+).

Workup

  1. customThe solvent was then removed by reduced pressure

Sources & evidence

ORD record
ord-f11c48013cad4a2d8ccc322bb074ed4f
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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