Hydrochloric Acid → HCID 58646900, compound

HRID 1244855Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.N1C(C)=CC=CC=1C.[N+:22]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[S:34](Cl)(=[O:36])=[O:35])([O-:24])=[O:23].Cl>ClCCl.O>[N+:22]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[S:34]([NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:36])=[O:35])([O-:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate (5 g, 27 mmol) was added to a solution of 2,6-lutidine (6.2 mL, 54 mmol) in dichloromethane (150 ml) under nitrogen. The reaction mixture was cooled down to 0° C. and a solution of 2,4-dinitrobenzenesulphonyl chloride (7.15 g, 27 mmol) in dichloromethane (100 ml) was slowly added over 15 minutes at 0° C. The reaction mixture was then stirred at room temperature for 48 hours under nitrogen. Water (100 ml) was added followed by 2N aqueous hydrogen chloride until the aqueous layer reached pH 2. The layers were then separated and the aqueous layer extracted with more dichloromethane (100 ml). The organic phases were combined, washed twice with water (100 ml), dried over magnesium sulfate and concentrated in vacuo to provide the title compound as a gum, 10 g (89%).

Workup

customThe layers were then separated
extractionthe aqueous layer extracted with more dichloromethane (100 ml)
washwashed twice with water (100 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-13442a2d859e4bf883c388a090389977
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122683B2

Reaction notes

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