Diisopropylethylamine → HCID 59260584, compound

HRID 643235Notes

Reaction equation

HRID 643235 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.[OH:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)[C:28](O)=[O:29].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>[OH:26][CH:27]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[C:28]([NH:16][CH2:15][CH2:14][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]#[CH:13])=[C:4]([O:3][CH3:2])[CH:5]=1)=[O:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576385742-Hydroxy-3-(4-methylphenyl)propanoic acidHCID 857743992-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine hydrochloride

Product 1

HCID 59260584HCID 59260584, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine hydrochloride (11.5 g, 47 mmol) and N,N-diisopropylethylamine (23 g, 0.18 mol) are dissolved in 100 ml of N,N-dimethylformamide. To this solution 2-hydroxy-3-p-tolyl-propionic acid (8.1 g, 45 mmol) and (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (22 g, 49 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 1:1) to afford 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide (E1.16).

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 1:1)

Sources & evidence

ORD record
ord-f9c9805c1ae24b8996d0a8c064be896f
Source dataset
uspto-grants-2010_04
Patent number
US07700522B2

Reaction notes

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