Diisopropylethylamine → HCID 57885066, compound

HRID 1818658Notes

Reaction equation

HRID 1818658 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15][NH2:16])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]#[CH:13].C(N(CC)C(C)C)(C)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:40])[CH2:34][CH:35]([OH:39])[C:36](O)=[O:37])=[CH:29][CH:28]=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:26][C:27]1[CH:28]=[CH:29][C:30]([C:33](=[O:40])[CH2:34][CH:35]([OH:39])[C:36]([NH:16][CH2:15][CH2:14][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]#[CH:13])=[C:4]([O:3][CH3:2])[CH:5]=2)=[O:37])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 30672534-(4-Chlorophenyl)-2-hydroxy-4-oxobutanoic acidHCID 85774399HCID 85774399, compound

Product 1

HCID 57885066HCID 57885066, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine hydrochloride (5.4 g, 22 mmol) and N,N-diisopropylethylamine (11 g, 83 mmol) are dissolved in 70 ml of N,N-dimethylformamide. To this solution 4-(4-chloro-phenyl)-2-hydroxy-4-oxo-butyric acid (4.8 g, 21 mmol) and (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (10 g, 23 mmol) are added successively. The reaction mixture is stirred for 16 hours at room temperature, subsequently poured on ice-water and extracted several times with ethyl acetate. The combined organic layer is washed with brine, dried over sodium sulfate and evaporated in vacuum. The remaining oil is purified by chromatography on silicagel (ethyl acetate/hexane 6:4) to give 4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-oxo-butyramide (Compound E1.10).

Workup

  1. additionsubsequently poured on ice-water
  2. extractionextracted several times with ethyl acetate
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuum
  6. customThe remaining oil is purified by chromatography on silicagel (ethyl acetate/hexane 6:4)

Sources & evidence

ORD record
ord-bfdbfcadb90a42bcad5e0b5236cc9b7d
Source dataset
uspto-grants-2009_10
Patent number
US07601674B2

Reaction notes

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