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

HRID 724659Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C@H:21]([NH:26]C(OC(C)(C)C)=O)[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][C:7]=1[CH:8]1[S:12](=[O:14])(=[O:13])[N:11](C(C)(C)C)[C:10](=[O:19])[CH2:9]1.[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].[NH2:26][C@@H:21]([CH2:20][C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[S:12](=[O:13])(=[O:14])[NH:11][C:10](=[O:19])[CH2:9]2)=[C:2]([Br:1])[CH:3]=1)[C:22]([O:24][CH3:25])=[O:23]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11692446Methyl (2S)-3-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-2-[(tert-butoxycarbonyl)amino]propanoate

Product 1

HCID 11670631Methyl (2S)-2-amino-3-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-propanoate Trifluoroacetate

Conditions

Temperature: 130 °C

Procedure

Methyl (2S)-3-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-2-[(tert-butoxycarbonyl)amino]propanoate (458 mg, 0.654 mmol) was dissolved in trifluoroacetic acid (10 mL) and heated at 130° C. in the microwave for 2 minutes. The solution was concentrated in vacuo to a white foam (420 mg, 99%). The product was used in subsequent steps without purification. 1H NMR (500 MHz, CDCl3): δ 7.68 (dd, J=14.2, 1.6 Hz, 1H), 7.56–7.51 (m, 1H), 7.40–7.36 (m, 1H), 5.65 (t, J=7.4 Hz, 1H), 4.39 (t, J=6.8 Hz, 1H), 3.82 (s, 3H), 3.47–3.42 (m, 1H), 3.36–3.25 (m, 2H), 2.18–3.11 (m, 1H); LCMS found for C13H16BrN2O5S (M+Na)+: m/z=391.

Workup

concentrationThe solution was concentrated in vacuo to a white foam (420 mg, 99%)
customThe product was used in subsequent steps without purification

Sources & evidence

ORD record: ord-b2826470a54343029d8ee8611bfa7744
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

Loading…