Diisopropylethylamine → 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide

HRID 992442Notes

Reaction equation

HRID 992442 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[NH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=1.C(N(C(C)C)C(C)C)C.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.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[C:10]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2212752-(3,4-Dichlorophenyl)-2-hydroxyacetic acidHCID 119576213-Methoxy-4-hydroxyphenylethylamine hydrochloride

Product 1

HCID 117730892-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of (3,4-dichloro-phenyl)-hydroxy-acetic acid (3 g), 4-(2-amino-ethyl)-2-methoxy-phenol hydrochloride (2.7 g) and ethyl-diisopropyl-amine (7 ml) in dimethylformamide (60 ml) is added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (6 g) in one portion. The mixture is stirred at room temperature for 3 hours. Then water (400 ml) is added. The mixture is extracted with ethyl acetate (2×400 ml) and washed with brine (2×200 ml). The organic layers are collected, dried with MgSO4 and evaporated. 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide is obtained which is purified by flash column chromatography on silica gel (ethyl acetate/hexane 2:1); the product is an oil.

Workup

  1. extractionThe mixture is extracted with ethyl acetate (2×400 ml)
  2. washwashed with brine (2×200 ml)
  3. customThe organic layers are collected
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-fb3b917320a7453fb3a75cd7c64f25c4
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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