Trifluoroacetic acid → Methyl (2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]-propanoate trifluoroacetate

HRID 724736Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:27])(=[O:26])[N:24](C(C)(C)C)[C:23](=[O:32])[CH2:22]2)=[C:17]([F:33])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:26])(=[O:27])[NH:24][C:23](=[O:32])[CH2:22]2)=[C:17]([F:33])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58746807Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]propanoate

Product 1

HCID 86602085Methyl (2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]-propanoate trifluoroacetateYield 61%

Procedure

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-isothiazolidin-5-yl)-3-fluorophenyl]propanoate (1.10 g, 2.26 mmol) in trifluoroacetic acid (10.0 mL) was heated for 2 minutes at 130° C. in the microwave. The solution was concentrated in vacuo and purified by preparative LCMS to afford product as a white solid (614 mg, 61%). 1H NMR (400 MHz, CD3OD): δ 7.53 (m, 1H), 7.18–7.14 (m, 2H), 5.33–5.30 (m, 1H), 4.39 (m, 1H), 3.82 (s, 3H), 3.43–3.12 (m, 4H). LCMS found for C13H16FN2O5S (M+H)+: m/z=331.

Workup

concentrationThe solution was concentrated in vacuo
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-f6188efa1f054c2786a971bc29f9d66e
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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