Triphenylphosphine → (R)-N-(2-aminopropyl)-N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide

HRID 333995Notes

Reaction equation

HRID 333995 reaction equation
O[CH2:2][C@H:3]([NH:5]C(=O)OC(C)(C)C)[CH3:4].[Cl:13][C:14]1[CH:34]=[CH:33][CH:32]=[CH:31][C:15]=1[CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[NH2:5][C@H:3]([CH3:4])[CH2:2][N:18]([CH2:17][CH2:16][C:15]1[CH:31]=[CH:32][CH:33]=[CH:34][C:14]=1[Cl:13])[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamateHCID 86699359N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 86699360(R)-N-(2-aminopropyl)-N-(2-chlorophenethyl)-2-nitrobenzenesulfonamideYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

740 mg of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate was dissolved in 30 mL of tetrahydrofuran in a nitrogen atmosphere, and 1.44 g of N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide and 3.3 g of triphenylphosphine were added thereto. 2.5 mL of diisopropyl azodicarboxylate was added thereto at 0° C., and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue (intermediate) was dissolved in 20 mL of dichloromethane. To the solution, 2 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 6 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane (30 mL×3). The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 380 mg of the title compound as a pale yellow oil (23%).

Workup

  1. additionwere added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe obtained residue (intermediate) was dissolved in 20 mL of dichloromethane
  4. additionTo the solution, 2 mL of trifluoroacetic acid was added
  5. stirringthe mixture was stirred at room temperature for 6 hours
  6. extractionfollowed by extraction with dichloromethane (30 mL×3)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-710a52c914cf4b758648659dd28a408b
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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