Hydrochloric Acid → HCID 86681707, compound

HRID 571300Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:22])[N:3]1[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25].Cl>O1CCOCC1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:22])[N:3]1[CH2:23][C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of tert-butyl 2-(1,3-dioxo-5-(N-(thiophen-2-ylmethyl)methylsulfonamido)isoindolin-2-yl)acetate (580 mg, 1.287 mmol) in dioxane (15 ml), aqueous 12M HCl (1 ml, 12.00 mmol) was added drop wise. The resulting mixture was stirred at 50° C. for 4 hours. The volatiles were removed under vacuum and the crude 2-(1,3-dioxo-5-(N-(thiophen-2-ylmethyl)methylsulfonamido) isoindolin-2-yl)acetic acid (490 mg, 1.242 mmol, 97% yield, MS/ESI+ 395.0 [MH]+). was used without further purification.

Workup

customThe volatiles were removed under vacuum

Sources & evidence

ORD record: ord-34a446eadf874ffab8109ad115c943a2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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