Sulfuryl chloride → HCID 49781658, compound

HRID 578577Notes

Reaction equation

HRID 578577 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:12][N:13]1[CH:17]=[C:16]([S:18](Cl)(=[O:20])=[O:19])[N:15]=[CH:14]1.S(Cl)(Cl)(=O)=O.CCN(C(C)C)C(C)C>CC#N>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][NH:11][S:18]([C:16]1[N:15]=[CH:14][N:13]([CH3:12])[CH:17]=1)(=[O:20])=[O:19])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 24648Sulfuryl chlorideHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride

Product 1

HCID 49781658HCID 49781658, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Mono-N-Boc-ethylenediamine (5; 5 g, 31.2 mmol, 1 eq) was sulfonylated with 1-methyl-1H-imidazole-4-sulfonyl chloride (6.76 g, 37.4 mmol, 1.2 eq). The appropriate sulfonyl chloride (1.2 equiv) was added to a solution of the amine (1 equiv) and DIPEA (2 equiv) in anhydrous CH3CN (0.1 M) at 0° C. The reaction was warmed to room temperature and stirred for 16 h, at which time the solvent was evaporated. The residue was re-dissolved in CH2Cl2, washed with 5% NaHCO3, water, brine, dried (Na2SO4), filtered and concentrated. After 16 h, the solvent was reduced and then the reaction mixture was dry-loaded onto silica gel and purified by flash column chromatography (eluent CH2Cl2/MeOH/NH4OH, 1092:7:1) to give the title compound as a white powder (9 g, 95%): δH (500 MHz, CD2Cl2) 1.37 (s, 9H, C(CH3)3), 2.99 (t, J=5.8 Hz, 2H, CH2NHSO2), 3.11 (q, J=5.8 Hz, 2H, CH2NHBoc), 3.71 (s, 3H, CH3), 5.53 (s, 1H, NHSO2), 5.68 (s, 1H, NHBoc), 7.48 (s, 1H, Im), 7.56 (s, 1H, Im); δC (125 MHz, CD2Cl2) 27.6, 33.5, 39.8, 42.6, 78.9, 124.0, 127.2, 139.2, 156.1; HRMS (ES+) calcd for [C11H20N4O4S+H] 305.1284. found 305.1294.

Workup

  1. customwas evaporated
  2. dissolutionThe residue was re-dissolved in CH2Cl2
  3. washwashed with 5% NaHCO3, water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. waitAfter 16 h
  8. custompurified by flash column chromatography (eluent CH2Cl2/MeOH/NH4OH, 1092:7:1)

Sources & evidence

ORD record
ord-8a14bc36396b48b8afdc9f7ebff5633e
Source dataset
uspto-grants-2015_05
Patent number
US09040563B2

Reaction notes

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