Hydrochloric Acid → (2S)-2-(1,1-Dioxidoisothiazolidin-2-yl)-4-methylpentanoic acid

Reaction equation

[O:1]=[S:2]1(=[O:19])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:8]([O:10]C(C)(C)C)=[O:9].Cl>>[O:1]=[S:2]1(=[O:19])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:8]([OH:10])=[O:9]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 66590788tert-Butyl(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanoate

Product 1

HCID 28166009(2S)-2-(1,1-Dioxidoisothiazolidin-2-yl)-4-methylpentanoic acid

Procedure

tert-butyl(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanoate (0.656 g, 2.251 mmol) from Step B was combined with HCl (4 N in dioxane, 5 mL, 20.00 mmol). The reaction mixture was stirred at room temperature for 24 hours, then the solvent removed in vacuo to furnish (2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanoic acid: MS (DCI+) m/z 253 (M+NH4)+.

Workup

customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-29557ca8c10547a1b84f0ab7badb9dd2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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