Triphenylphosphine → t-Butyl (2-{4-[3-(4-tolyl-sulfonylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

HRID 1180810

反応式

HRID 1180810 の反応式
[C:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(OC(C)(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.OC[CH:40]=[CH:41][C:42]1[CH:64]=[CH:63][C:45]([C:46]([NH:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:47])=[CH:44][CH:43]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:15]1([CH3:18])[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH2:1][CH:40]=[CH:41][C:42]2[CH:64]=[CH:63][C:45]([C:46]([NH:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[NH:55][C:56](=[O:62])[O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:47])=[CH:44][CH:43]=2)(=[O:10])=[O:11])=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688170N-Boc-p-toluenesulfonamideHCID 72479808t-Butyl {2-[4-(3-hydroxy-propenyl)-benzoylamino]-phenyl}-carbamate

生成物 1

HCID 86602774t-Butyl (2-{4-[3-(4-tolyl-sulfonylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of N-Boc-4-tolylsulfonamide (221 mg, 0.81 mmol) and PPh3 (427 mg, 1.63 mmol) in anhydrous THF (4 ml) under nitrogen was successively added a solution of compound XVIII (200 mg, 0.54 mmol) in anhydrous THF (1 ml) and diethyl azodicarboxylate (DEAD) (214 μl, 1.36 mmol). After 16 h, the reaction mixture was quenched with water and diluted with AcOEt. After separation the organic layer was successively washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60) to afford the title compound XVIIg (337 mg).

後処理

  1. customthe reaction mixture was quenched with water
  2. additiondiluted with AcOEt
  3. customAfter separation the organic layer
  4. washwas successively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60)

出典と根拠

ORDレコード
ord-57d4d008feba4e459f148af7837eafeb
出典データセット
uspto-grants-2007_10
特許番号
US07282608B2

関連ノート

読み込み中…