4-Chloromandelic acid → 2-(4-Chloro-phenyl)-2-hydroxy-n-(3-methoxy-4-pent-2-ynyloxy-benzyloxy)-acetamide

HRID 458248

反応式

HRID 458248 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]#[C:15][CH2:16][CH3:17])[CH2:6][O:7][NH2:8].C(N(C(C)C)C(C)C)C.[Cl:27][C:28]1[CH:38]=[CH:37][C:31]([CH:32]([OH:36])[C:33](O)=[O:34])=[CH:30][CH:29]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([CH:32]([OH:36])[C:33]([NH:8][O:7][CH2:6][C:5]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]#[C:15][CH2:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:34])=[CH:37][CH:38]=1

参加物

6

反応物 4

HCID 102994-Chloromandelic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18442094O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine

生成物 1

HCID 184420662-(4-Chloro-phenyl)-2-hydroxy-n-(3-methoxy-4-pent-2-ynyloxy-benzyloxy)-acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine (5.0 g, 21 mmol) and N-ethyldiisopropylamine (Hünig's base, 5.5 g, 42 mmol) are dissolved in 60 ml of N,N-dimethylformamide. 4-chloro-DL-mandelic acid (4.1 g, 22 mmol) and (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, Castro's reagent, 10 g, 23 mmol) are added successively and the mixture is stirred for 16 h. After pouring the mixture on ice/water, it is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane (4:6)) to obtain 2-(4-chloro-phenyl)-2-hydroxy-N-(3-methoxy-4-pent-2-ynyloxy-benzyloxy)-acetamide as yellow resin.

後処理

  1. additionAfter pouring the mixture on ice/water, it
  2. extractionis extracted with ethyl acetate
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane (4:6))

出典と根拠

ORDレコード
ord-921bf4a08a354f3580fa42e39bc8b254
出典データセット
uspto-grants-2007_03
特許番号
US07189873B2

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