Trifluoroacetic acid → HCID 58746580, compound

HRID 724648Notes

Reaction equation

C([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:28]=[CH:27][C:14]([CH2:15][C:16]3([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]3)=[CH:13][CH:12]=2)[S:6]1(=[O:30])=[O:29])(C)(C)C.FC(F)(F)C(O)=O>>[O:30]=[S:6]1(=[O:29])[CH:7]([C:11]2[CH:28]=[CH:27][C:14]([CH2:15][C:16]3([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]3)=[CH:13][CH:12]=2)[CH2:8][C:9](=[O:10])[NH:5]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58746877HCID 58746877, compound

Product 1

HCID 58746580HCID 58746580, compoundYield 84.3%

Conditions

Temperature: 130 °C

Procedure

Ethyl 2-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-5-oxopyrrolidine-2-carboxylate (34 mg, 0.078 mmol) was stirred in trifluoroacetic acid (3.0 mL, 40.0 mmol) in a small microwave tube and heated to 130° C. for 60 seconds. Trifluoroacetic acid was evaporated and the residue was purified by preparative LCMS to give the desired compound as a white solid (25 mg, 84%). 1H-NMR (400 MHz, CD3OD): δ 7.45 (d, J=8.2 Hz, 2H), 7.32 (d, J=8.2 Hz, 2H), 5.17 (t, J=8.9 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 3.30 (m, 2H), 3.20 (d, J=13.6 Hz, 1H), 3.10 (d, J=13.6 Hz, 1H), 2.38 (m, 1H), 2.21 (m, 2H), 1.95 (m, 1H), 1.23 (t, J=7.0 Hz, 3H); LCMS found for C17H21N2O6S (M+H)+: m/z=381.

Workup

customTrifluoroacetic acid was evaporated
customthe residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-e5ed19bc285148f3ba6cb94a9fa24a09
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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