Diisopropylethylamine → HCID 18412024, compound

HRID 992454Notes

Reaction equation

HRID 992454 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:15][CH2:16][NH2:17])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]#[C:13]C.C(N(C(C)C)C(C)C)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([OH:39])([CH3:38])[C:35](O)=[O:36])=[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>>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([OH:39])([CH3:38])[C:35]([NH:17][CH2:16][CH2:15][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:36])=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 100130442-(4-chlorophenyl)-2-hydroxypropanoic acidHCID 18412037HCID 18412037, compound

Product 1

HCID 18412024HCID 18412024, compound

Procedure

To a stirred solution of 906 mg of 2-(3-methoxy-4-but-2-ynyloxy-phenyl)-ethylamine hydrochloride and 2.75 ml N-ethyldiisopropylamine are subsequently added 752 mg 2-(4-chlorophenyl)-2-hydroxy propionic acid and 1.875 g benzotriazole-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate. The resulting clear solution is stirred over night, extracted with ethyl acetate. The extracts are washed several times with water, dried over sodium sulfate, filtered and evaporated. The resulting oily residue is purified on silicagel (hexanc ethyl acetate) to obtain the 2-(4-chlorophenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]propionamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts are washed several times with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oily residue is purified on silicagel (hexanc ethyl acetate)

Sources & evidence

ORD record
ord-33d0651326b04c7ebd7f11319889126b
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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