Sodium Chloride → 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide

HRID 1375226Notes

Reaction equation

HRID 1375226 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]([OH:9])[C:6]([OH:8])=O.[NH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=1.C(N(CC)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.[Cl-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:9])[C:6]([NH:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=2)=[O:8])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2212752-(3,4-Dichlorophenyl)-2-hydroxyacetic acidHCID 58785260trans-4-(2-Amino-cyclohexyl)-2-methoxy-phenol

Product 1

HCID 115390922-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3.09 g (13.5 mmol) of DL-3,4-dichloromandelic acid, 3.0 g (13.5 mmol) of trans-4-(2-amino-cyclohexyl)-2-methoxy-phenol and 1.89 (13.5 mmol) of N,N-diisopropylethylamine in 30 ml DMF is added 6.0 g (13.5 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate in one portion. The reaction mixture is then stirred at ambient temperature for about 2 hours and thereafter poured into 150 ml of aqueous saturated sodium chloride solution. The two-phase mixture is extracted with two 150 ml portions of ethyl acetate. The organic extract is concentrated under reduced pressure to a residue, which is subjected to column chromatography on silica gel, with 1:1 ethyl acetate/isohexane as the eluant yielding 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide.

Workup

  1. extractionThe two-phase mixture is extracted with two 150 ml portions of ethyl acetate
  2. extractionThe organic extract
  3. concentrationis concentrated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-db21735ac61445d8a0ce8c70c87a36ea
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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