Triethylamine → tert-butyl {[((2R)-1,4-dioxan-2-ylmethyl)(methyl)amino]sulfonyl}carbamate

HRID 1987100Notes

Reaction equation

HRID 1987100 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][NH:9][CH3:10].[C:11]([O:15][C:16]([NH:18][S:19](N1C=CC(=[N+](C)C)C=C1)(=[O:21])=[O:20])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[O:2]1[CH2:7][CH2:6][O:5][CH2:4][C@H:3]1[CH2:8][N:9]([CH3:10])[S:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])(=[O:20])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66972118(1,4-Dioxan-2-ylmethyl)methylamine hydrochlorideHCID 178482963HCID 178482963, compound

Product 1

HCID 53309829tert-butyl {[((2R)-1,4-dioxan-2-ylmethyl)(methyl)amino]sulfonyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1,4-dioxan-2-yl)-N-methylmethanamine hydrochloride (0.760 g, 4.55 mmol), N-[1-{[(tert-butoxycarbonyl)amino]sulfonyl}pyridin-4(1H)-ylidene]-N-methylmethanaminium (1.51 g, 5.00 mmol), and triethylamine (1.55 mL, 11.4 mmol) were slurried in 50 mL dichloromethane and stirred at ambient temperature. After 12 hours, the solution was concentrated in vacuo and purified by silica chromatography (50-100% ethyl acetate/hexanes gradient) to afford the title compound. LRMS (APCI) calc'd for (C11H22N2O6SNa) [M+Na]+, 333.1; found, 333.1.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by silica chromatography (50-100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-2672778e0eee457c9cc1f36f41bb9933
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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