(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 59532373, compound
Reaction equation
[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([N:26]2[CH2:31][CH2:30][C@:29]([CH2:38][C:39](O)([CH3:41])[CH3:40])([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:28][C:27]2=[O:43])[CH3:25])=[CH:20][CH:19]=1>O1CCCC1.C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([C@@H:24]([N:26]2[CH2:31][CH2:30][C@@:29]([CH2:38][C:39]([CH3:41])=[CH2:40])([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:28][C:27]2=[O:43])[CH3:25])=[CH:22][CH:23]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
(Methoxycarbonylsulfamoyl)triethylammonium hydroxide (1.38 g) was added to 3-[(S)-1-(4-bromo-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (2.0 g) dissolved in tetrahydrofuran (30 mL) and toluene (15 mL). The resulting solution was stirred at room temperature for 0.5 h and at 75° C. for 1 h. After cooling to room temperature, the solution was concentrated and ethyl acetate was added to the residue. The resulting mixture was washed with aqueous NaHCO3 solution and brine and dried (MgSO4). The title compound was obtained after removal of the solvent. Yield: 1.9 g (quantitative). Mass spectrum (ESI+): m/z=414/416 (Br) [M+H]+
Workup
- temperatureAfter cooling to room temperature
- concentrationthe solution was concentrated
- additionethyl acetate was added to the residue
- washThe resulting mixture was washed with aqueous NaHCO3 solution and brine
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-26f2170aefd34aa09444b15761c9b9a4
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754076B2
Reaction notes
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