tert-Butanol → HCID 10636611, compound
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].Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(N(CC)CC)C>ClCCl>[C:8]([O:12][C:6]([NH:5][S:2]([NH:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20])(=[O:4])=[O:3])=[O:7])([CH3:11])([CH3:10])[CH3:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of chlorosulfonylisocyanate (Sigma-Aldrich) (5.0 mL, 57.4 mmol) in dichloromethane (100 mL) was cooled to 0° C. Tert-butyl alcohol (4.26 g, 57.4 mmol, 1.0 equiv.) was added dichloromethane (100 mL) via an addition funnel. This solution was stirred at 0° C. for 30 min. Glycine ethyl ester hydrochloride (8.82 g, 63.2 mmol, 1.1 equiv.) was added followed by drop-wise addition of triethylamine (20.0 mL, 144 mmol, 2.5 equiv.) at 0° C. This reaction mixture was stirred at room temperature for 4 h. The reaction was diluted with dichloromethane (100 mL) and washed with 0.1 N hydrochloric acid and brine. The organic layer was dried over sodium sulfate and concentrated to give the desired product (13.2 g, 81.4%) as a crude off-white solid, which was used in the subsequent reaction without further purification. 1H NMR (300 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.07 (t, 1H, J=6.1 Hz), 4.08 (q, 2H, J=7.1 Hz), 3.78 (d, 2H, J=6.1 Hz), 1.40 (s, 9H), 1.18 (t, 3H, J=7.1 Hz).
Workup
- stirringThis reaction mixture was stirred at room temperature for 4 h
- washwashed with 0.1 N hydrochloric acid and brine
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7a12830ed3084d6f83840b3312e5679c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321755B2
Reaction notes
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