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Triphenylphosphine → N-[(2R)-2-amino-2-phenylethyl]-N-methyl-2-nitrobenzenesulfonamide

HRID 64411
Notes
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Reaction equation

HRID 64411 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:5])=[O:4].O[CH2:16][C@H:17]([NH:24]C(=O)OC(C)(C)C)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[NH2:24][C@H:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][N:2]([CH3:1])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:4])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 264906N-methyl-2-nitrobenzene-1-sulfonamideHCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 86713419N-[(2R)-2-amino-2-phenylethyl]-N-methyl-2-nitrobenzenesulfonamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1 g of N-methyl-2-nitrobenzenesulfonamide, 2.3 g of tert-butyl [(1R)-2-hydroxy-1-phenylethyl]carbamate, 2.5 g of triphenylphosphine, 4.2 ml of diethyl azodicarboxylate, and 40 ml of toluene was stirred at 80° C. for 2 hours, and the solvent was evaporated under reduced pressure. To a solution of the obtained residue in chloroform was added silica gel, followed by filtration, and the filtrate was concentrated under reduced pressure. To a solution of the obtained residue in 3 ml of dichloromethane was added 3 ml of trifluoroacetic acid, followed by stirring for 1 hour. The solvent was evaporated under reduced pressure, and an aqueous sodium carbonate solution and chloroform were then added thereto to carry out a layer separation operation. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 890 mg of N-[(2R)-2-amino-2-phenylethyl]-N-methyl-2-nitrobenzenesulfonamide.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo a solution of the obtained residue in chloroform was added silica gel
  3. filtrationfollowed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo a solution of the obtained residue in 3 ml of dichloromethane was added 3 ml of trifluoroacetic acid
  6. stirringby stirring for 1 hour
  7. customThe solvent was evaporated under reduced pressure
  8. additionan aqueous sodium carbonate solution and chloroform were then added
  9. customa layer separation operation
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c5c537016d084789ab8e0494cad95146
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447090B2

Reaction notes

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