Water → HCID 22851705, compound

HRID 55455Notes

Reaction equation

[OH:1][C:2]1[C:3]([O:5][C@H:6]([CH3:12])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14].CN1CCOCC1.O>C1(C)C=CC=CC=1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([O:1][C:2]2[C:3]([O:5][C@H:6]([CH3:12])[C:7]=2[C:8]([O:10][CH3:11])=[O:9])=[O:4])(=[O:24])=[O:23])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

Conditions

Temperature: 5 °C

Procedure

34.44 g of (R)-2-hydroxy-3-methoxycarbonyl-2-penten-4-olide are dissolved in 170 ml of toluene at 40° C., 49.4 g of p-nitrobenzenesulphonyl chloride in 160 ml of toluene are added and the whole is cooled to 5° C. Within a period of 30 minutes, 20.3 g of N-methylmorpholine are metered in at from 0 ° to 5° C. 350 ml of water are added, the toluene product phase is removed, and the aqueous phase is re-extracted twice with 100 ml of toluene. The toluene phases are washed with sodium chloride solution and with water, filtered over a small amount of silica gel and concentrated by evaporation. The residue is crystallised from ethyl acetate/cyclohexane. [α]D20 =+12.4° (3% in CHCl3), m.p. 123°-124° C.

Workup

customare metered in at from 0 ° to 5° C
customthe toluene product phase is removed
extractionthe aqueous phase is re-extracted twice with 100 ml of toluene
washThe toluene phases are washed with sodium chloride solution and with water
filtrationfiltered over a small amount of silica gel
concentrationconcentrated by evaporation
customThe residue is crystallised from ethyl acetate/cyclohexane
custom[α]D20 =+12.4° (3% in CHCl3), m.p. 123°-124° C.

Sources & evidence

ORD record: ord-a08739a82bba4499bfe0ebe981bdd7ec
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05625059

Reaction notes

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