Trifluoroacetic acid → HCID 11568380, compound

HRID 724716Notes

Reaction equation

C(OC([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[S:28](=[O:30])(=[O:29])[N:27](C(C)(C)C)[C:26](=[O:35])[CH2:25]2)=[C:20]([CH3:36])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])=O)C1C=CC=CC=1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[NH2:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:35])[CH2:25]2)=[C:20]([CH3:36])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11599846HCID 11599846, compound

Product 1

HCID 11568380HCID 11568380, compoundYield 74%

Procedure

A solution of methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-methylphenyl]propanoate (450 mg, 0.871 mmol) in trifluoroacetic acid (3.00 mL) was heated in microwave reactor at 130° C. for 5 min. Solvent was removed in vacuo. The residue was purified with preparative LCMS to give the desired product (210 mg, 74%). 1H NMR (400 MHz, CD3OD): δ 7.45 (m, 1H), 7.2 (m, 2H), 5.47 (t, 1H), 4.34 (t, 1H), 3.81 (s, 3H), 3.3 (m, 2H), 3.25 (d, 1H), 3.13 (m, 1H), 2.49 (s, 3H); MF=C14H19N2O5S; LCMS found for C14H20N2O5S (M+H)+: m/z=327.

Workup

customSolvent was removed in vacuo
customThe residue was purified with preparative LCMS

Sources & evidence

ORD record: ord-6c910287e809486bbacbedbc23d2a8f0
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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