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

HRID 458248

Reaction equation

HRID 458248 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-921bf4a08a354f3580fa42e39bc8b254
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Linked notes

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