Triphenylphosphine → HCID 23121847, compound

HRID 1713504Notes

Reaction equation

HRID 1713504 reaction equation
[CH:1]1([CH2:4][NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH2:3][CH2:2]1.O[CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[NH2:21][CH2:20][CH2:19][N:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 21701822HCID 21701822, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 23121847HCID 23121847, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of N-(cyclopropylmethyl)-2-nitrobenzenesulfonamide (1.7 g, 6.4 mmol), t-butyl N-(2-hydroxyethyl)carbamate (1.3 g, 8.3 mmol) and triphenylphosphine (2.2 g, 8.3 mmol) in toluene (20 mL) was added a 40% solution of diethyl azodicarboxylate in toluene (3.6 g, 8.3 mmol) with ice cooling, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure to a half its original volume, and diethyl ether (30 mL) was added thereto. The precipitates were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=49:1 to hexane:ethyl acetate=1:1) to obtain a condensed compound as an oily matter. A 4 M hydrogen chloride/ethyl acetate solution (20 mL) was added thereto, and the mixture was stirred at room temperature for 30 minutes. To the reaction solution was added water (70 mL) and extracted. The aqueous layer was collected by separation and washed with ethyl acetate. The aqueous layer was basified with a 4 N aqueous sodium hydroxide solution (pH=12), and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=19:1 to ethyl acetate) to obtain the title compound (1.2 g, yield 62%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure to a half its original volume, and diethyl ether (30 mL)
  2. additionwas added
  3. filtrationThe precipitates were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=49:1 to hexane:ethyl acetate=1:1)
  6. customto obtain a condensed compound as an oily matter
  7. stirringthe mixture was stirred at room temperature for 30 minutes
  8. extractionextracted
  9. customThe aqueous layer was collected by separation
  10. washwashed with ethyl acetate
  11. extractionextracted with ethyl acetate
  12. dry with materialThe extract was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=19:1 to ethyl acetate)

Sources & evidence

ORD record
ord-467896218a8141a39073362be3312b0c
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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