Triphenylphosphine → HCID 59372566, compound

HRID 1966416Notes

Reaction equation

HRID 1966416 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][NH:8][S:9]([NH:12][C:13](=O)OC(C)(C)C)(=[O:11])=[O:10])([O-:3])=[O:2].[C:23]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][NH:8][S:9]([NH:12][CH2:13][CH3:23])(=[O:11])=[O:10])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57515616HCID 57515616, compound

Product 1

HCID 59372566HCID 59372566, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Crude tert-butyl N-(3-nitrobenzylsulfamoyl)carbamate, triphenylphosphine (2 g) and diisopropyl azodicarboxylate (DIAD, 1.6 g) were dissolved in THF (20 mL) and ethanol (0.47 ml). The solution was stirred at ambient temperature overnight. The reaction solution was evaporated to dryness. The residue was dissolved in methanol (10 mL) and treated with 4.0 M HCl in dioxane (10 mL). It was stirred at rt overnight and then evaporated. The residue was diluted with ethyl acetate (100 mL) and washed with NaHCO3 aq. (2×100 mL). The organic solution was evaporated and purified by flash column chromatography (EtOAc/hexane=1/2, 1/1) to give N-(3-nitrobenzyl)-N′-ethylsulfamide. 1H NMR (DMSO-d6): δ 1.02 (t, J=7.2 Hz, 3H), 2.82 (p, J=6.9 Hz, 2H), 4.14 (d, J=6.6 Hz, 2H), 6.93 (t, J=5.4 Hz, 1H), 7.54 (t, J=6.3 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.77 (d, J=7.2 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 8.20 (s, 1H); LCMS: purity: 1.2 g, 88.4%; MS (m/e): 260.16 (MH+).

Workup

  1. customThe reaction solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. additiontreated with 4.0 M HCl in dioxane (10 mL)
  4. stirringIt was stirred at rt overnight
  5. customevaporated
  6. additionThe residue was diluted with ethyl acetate (100 mL)
  7. washwashed with NaHCO3 aq. (2×100 mL)
  8. customThe organic solution was evaporated
  9. custompurified by flash column chromatography (EtOAc/hexane=1/2, 1/1)

Sources & evidence

ORD record
ord-1e533661fd7145bbb3b75ce8fb3eb709
Source dataset
uspto-grants-2013_04
Patent number
US08420659B2

Reaction notes

Loading…