Ethanamine, 2-fluoro-, hydrochloride → 5-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-(2-fluoroethyl)isoxazole-3-carboxamide

HRID 880355ノート

反応式

HRID 880355 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38](O)=[O:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:64][CH2:65][CH2:66][NH2:67].CCN(C(C)C)C(C)C>C1COCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([NH:67][CH2:66][CH2:65][F:64])=[O:39])[CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667591895-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acid

生成物 1

HCID 866623755-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-(2-fluoroethyl)isoxazole-3-carboxamide収率 94%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acid (0.45 g, 0.84 mmol) in THF (30 mL) was added TBTU (0.300 g, 1.1 mmol). After stirring for 15 minutes at room temperature, 2-fluoroethylamine hydrochloride (0.1 g, 1 mmol) and DIPEA (0.58 mL) were subsequently added. After stirring overnight, the suspension was diluted with DCM and washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 3/1, to provide the title compound (0.46 g, 94% yield).

後処理

  1. stirringAfter stirring overnight
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 3/1

出典と根拠

ORDレコード
ord-69cf9b3146ae4fb8a0ee8eeeea5c5e93
出典データセット
uspto-grants-2015_03
特許番号
US08993556B2

反応ノート

読み込み中…