Triethylamine → 3-(3-(4-(Tert-butyl)phenyl)ureido)propyl methanesulfonate

HRID 2284544Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-tert-butylphenyl)-3-(3-hydroxypropyl)urea (563 mg, 2.25 mmol) in methylene chloride (14 mL) was cooled at 0° C. and treated dropwise with triethylamine (0.376 mL, 2.70 mmol) followed by methanesulfonyl chloride (0.191 mL, 2.47 mmol) and the mixture was stirred at 0° C. until complete by TLC. After 30 minutes, the reaction was complete by TLC (100% EA). The reaction mixture was diluted with 15 mL CH2Cl2 and the organic phase was washed with 15 mL portions of 1N HCl, sat NaHCO3 and H2O and dried over MgSO4. The solution was filtered and concentrated to a viscous oil that was placed under high vacuum to yield the title compound (800 mg) as a colorless viscous oil that was stored in the freezer: MS (ESI+) for C15H24N2O4S m/z 329.1 (M+H)+; HPLC purity 93% (ret. time, 3.95 min).

Workup

washthe organic phase was washed with 15 mL portions of 1N HCl
dry with materialdried over MgSO4
filtrationThe solution was filtered
concentrationconcentrated to a viscous oil that

Sources & evidence

ORD record: ord-c0ea24202e384a348c60bd3760b77a8c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145438B2

Reaction notes

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