Water → HCID 178427310, compound

HRID 1655635Notes

Reaction equation

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

Participants

Conditions

Temperature: -5 °C

Procedure

(S)-2-(p-Toluenesulfonylamino)-1,4-butanediol, 2, (46 g) was dissolved in methylene chloride (450 mL) and triethylamine (60 g) was added. The resulting solution was cooled to -5° C. under a nitrogen atmosphere and a solution of methanesulfonyl chloride (42.0 g) in methylene chloride (110 mL) was added dropwise over 3 hours. The resulting mixture was stirred an additional 0.5 hour at 0° to -5° C. and water (150 mL) and methylene chloride (350 mL) were cautiously added. The layers were separated and the organic layer extracted with 0.1N HCl (100 mL) and demineralized water (100 mL) and then concentrated under vacuum to give (S)-2-(2'-methanesulfonyloxyethyl)-1-(p-toluenesulfonyl)aziridine, 3, as a light yellow solid (57.2 g) which was used directly in the next step without further purification. A portion was recrystallized from ethyl acetate and hexanes: mp 78°-80° C.

Workup

customThe layers were separated
extractionthe organic layer extracted with 0.1N HCl (100 mL) and demineralized water (100 mL)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b57210fb63c846e28ccdc4a3b3a32369
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250704

Reaction notes

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