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

HRID 64411
ノート
印刷プレビュー

反応式

HRID 64411 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c5c537016d084789ab8e0494cad95146
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447090B2

反応ノート

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