4-Methylmorpholine → HCID 71489277, compound

HRID 2167411Notes

Reaction equation

[OH:1][CH2:2][C@@H:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH3:4].CN1CCOCC1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH2:2][C@@H:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:7])=[O:8])[CH3:4])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)—N-(1-hydroxypropan-2-yl)-2-nitrobenzenesulfonamide (6.20 kg, 23.8 mol) in methylene chloride (32 L) was added 4-methylmorpholine (3.13 kg, 30.9 mol) at an internal temperature of 10° C. or below. The resulting reaction mixture was cooled to 0° C., and added a solution of methanesulfonyl chloride (3.27 kg, 28.5 mol) in methylene chloride (2 L) at an internal temperature of −5° C. to 0° C. Subsequently, the reaction mixture was stirred at room temperature for 20 hours. After confirming the disappearance of the starting materials by TLC, purified water was added to the reaction mixture. The resulting organic layer was partitioned, washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the target product as a yellow solid (7.30 kg, yield 90.70).

Workup

customThe resulting reaction mixture
custompurified water
additionwas added to the reaction mixture
customThe resulting organic layer was partitioned
washwashed with saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-b2694fcd1721433aa2d07a1b7e562071
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045460B2

Reaction notes

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