(4-Chlorophenyl)acetic acid → HCID 23446817, compound

HRID 1841644Notes

Reaction equation

HRID 1841644 reaction equation
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:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=O)=[CH:31][CH:30]=1.[C:39]([O:47][NH:48][CH2:49][CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][CH2:58][C:59]#[CH:60])=[C:53]([O:61][CH3:62])[CH:52]=1)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[C:39]([O:47][N:48]([CH2:49][CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][CH2:58][C:59]#[CH:60])=[C:53]([O:61][CH3:62])[CH:52]=1)[C:36](=[O:38])[CH2:35][C:32]1[CH:31]=[CH:30][C:29]([Cl:28])=[CH:34][CH:33]=1)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 15880(4-Chlorophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23446812HCID 23446812, compound

Product 1

HCID 23446817HCID 23446817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

BOP (2.0 g, 4.5 mmol) is added to a solution of (4-chloro-phenyl)-acetic acid (0.7 g, 4.1 mmol), N-benzoyloxy-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine (1.4 g, 4.3 mmol) and N-ethyldiisopropylamine (2.8 ml, 16.4 mmol) in 10 ml DMF. The reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into water and extracted three times with ethyl acetate. The organic phase is dried over Na2SO4 and concentrated. The crude product is purified by flash chromatography (ethyl acetate:hexane, 1:3) to yield N-benzoyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide as an oil.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product is purified by flash chromatography (ethyl acetate:hexane, 1:3)

Sources & evidence

ORD record
ord-b835351889b542c18f50d33098d1649a
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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