Methanesulfonyl chloride → 6-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate

HRID 857092Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][S:27]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:14]=1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: 20 °C

Procedure

3-(3-{4-[(6-Hydroxyhexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione (2.67 g) in CH2Cl2 (50 ml) and triethylamine (1.2 ml) was treated with methanesulfonyl chloride (1.22 ml) and the mixture was stirred at 20° C. for 1.5 h. The mixture was diluted with CH2Cl2 and washed with 2M HCl, NaHCO3, dried and purified by chromatography on Biotage (40 g) eluting with EtOAc-petroleum ether(1:1) and then with 2% MeOH—CH2Cl2 to give the title compound (1.186 g) ES+ve 427 (MH)+.

Workup

washwashed with 2M HCl, NaHCO3
customdried
custompurified by chromatography on Biotage (40 g)
washeluting with EtOAc-petroleum ether(1:1)

Sources & evidence

ORD record: ord-74b489f74d41402bbbecfba635ba734c
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144908B2

Reaction notes

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