Triethylamine → N-t-butoxycarbonyl-N'-thiomorpholinocarbonyl-N,N'-dimethylethylenediamine

HRID 2396147Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][CH2:10][NH:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:14]1[CH2:19][CH2:18][N:17]([C:20](Cl)=[O:21])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][CH2:10][N:11]([C:20]([N:17]1[CH2:18][CH2:19][S:14][CH2:15][CH2:16]1)=[O:21])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

N-t-Butoxycarbonyl-N,N'-dimethylethylenediamine (200 mg) was added to a solution of thiomorpholinocarbonyl chloride (228 mg) and triethylamine (123 mg) in methylene chloride (10 ml) which was cooled at 0° C. The mixture was stirred at ambient temperature for 20 minutes and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 0.6N hydrochloric acid, water, saturated sodium bicarbonate solution, and saturated sodium chloride solution successively, dried over magnesium sulfate, and concentrated under reduced pressure to give N-t-butoxycarbonyl-N'-thiomorpholinocarbonyl-N,N'-dimethylethylenediamine (376 mg) as an oil. Rf: 0.43 (chloroform:methanol, 10:1, V/V)

Workup

customthe solvent was evaporated in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washthe solution was washed with 0.6N hydrochloric acid, water, saturated sodium bicarbonate solution, and saturated sodium chloride solution successively
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-47d58aed63484998ac2f95304588ffd9
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491132

Reaction notes

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