Hydrochloric Acid → HCID 86681710, compound

HRID 571303Notes

Reaction equation

[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][N:5]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:13]2=[O:28])[S:6]([CH3:9])(=[O:8])=[O:7].[ClH:30]>O1CCOCC1>[ClH:30].[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][N:5]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][C:21]([OH:23])=[O:22])[C:13]2=[O:28])[S:6]([CH3:9])(=[O:8])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 2-(5-(N-(2-(dimethylamino)ethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (300 mg, 0.705 mmol) in dioxane (8 ml), 4M HCl in dioxane (1.763 ml, 7.05 mmol) was added, and the mixture was heated under microwave irradiation at 100° C. for 2 hours. The volatiles were removed under vacuum and the crude was purified by trituration with Et2O affording after filtration 2-(5-(N-(2-(dimethylamino)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid hydrochloride (250 mg, 0.616 mmol, 87% yield), MS/ESI+ 370.0 [MH]+).

Workup

customThe volatiles were removed under vacuum
customthe crude was purified by trituration with Et2O affording

Sources & evidence

ORD record: ord-1edc729a230f48028b801f8eee0480b0
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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