Diisopropylethylamine → HCID 18412024, compound

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

Reactant 4

HCID 81531Diisopropylethylamine

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

HCID 100130442-(4-Chlorophenyl)-2-hydroxypropanoic acid

HCID 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.