Hydrochloric Acid → HCID 118059919, compound

HRID 632535Notes

Reaction equation

Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17].C(N(CC)CC)C.Cl>ClCCl>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:17][S:2]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of chlorosulfonylisocyanate (11.32 g, 80 mmol) in dichloromethane (120 mL) was cooled to 0° C. Tert-butyl alcohol (7.65 mL, 80.0 mmol, 1.0 equiv.) was added via addition funnel. The mixture was stirred at 0° C. for 1.5 h. To this mixture, a solution of aminoacetaldehyde dimethyl acetal (8.76 mL, 80.0 mmol, 1.0 equiv.) and triethylamine (TEA, 33.4 mL, 240 mmol, 3.0 equiv.) in methylene chloride (DCM 120.0 mL) was added drop-wise via addition funnel. The reaction was warmed to room temperature and stirred overnight. The reaction was treated with 0.1 N hydrochloric acid and the organic layer was washed with brine, dried over sodium sulfate and concentrated to give the desired product (15.6 g, 68.5%) as a crude off-white solid, which was used for the subsequent reaction without further purification: 1H NMR (300 MHz, DMSO-d6) δ 10.84 (s, 1H), 7.62 (t, 1H, J=6.0 Hz), 4.38 (t, 1H, J=5.5 Hz), 3.24 (s, 6H), 2.96 (dd, 2H, J=5.8 Hz), 1.41 (s, 9H).

Workup

additionvia addition funnel
temperatureThe reaction was warmed to room temperature
stirringstirred overnight
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-8ca82d3216564ed6b93eee65c41833dd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321755B2

Reaction notes

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