Trifluoroacetic acid → HCID 86602084, compound

HRID 724722Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@@H:10]([NH:30][C:31]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:32])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[S:22](=[O:24])(=[O:23])[N:21](C(C)(C)C)[C:20](=[O:29])[CH2:19]2)=[CH:14][CH:13]=1.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C@@H:10]([NH:30][C:31]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:32])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:29])[CH2:19]2)=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58746505HCID 58746505, compound

Product 1

HCID 86602084HCID 86602084, compoundYield 34%

Procedure

A solution of ethyl [((1S)-1-(1h-benzimidazol-2-yl)-2-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]ethylamino)carbonyl]aminoacetate (4 mg, 7.20 μmol) and trifluoroacetic acid (1.50 mL) was heated at 120° C. for 5 min in the microwave. The reaction concentrated in vacuo and purified by preparative LCMS to yield the desired product (1.5 mg, 34%). 1H NMR (400 MHz, CD3OD): δ 7.7 (m, 2H), 7.6 (m, 2H), 7.5 (m, 2H), 7.3 (m, 2H), 5.3 (m, 1H), 5.2 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5–3.3 (m, 4H), 1.2 (t, 3H); MF=C25H26F3N5O8S; LCMS found for C23H26N5O6S (M+H)+: m/z=500.

Workup

concentrationThe reaction concentrated in vacuo
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-cb9d3536700245aca65cf997a1a81f7a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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