Triphenylphosphine → HCID 59372566, compound

HRID 2387186Notes

Reaction equation

HRID 2387186 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>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

5

Reactant 2

HCID 11776TriphenylphosphineHCID 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 azadicarboxylate (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-719ec82f0f854f09ac544068b8d34677
Source dataset
uspto-grants-2012_09
Patent number
US08268851B2

Reaction notes

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