Water → HCID 12049888, compound

HRID 2185026Notes

Reaction equation

HRID 2185026 reaction equation
[NH2:1][C@@H:2]([CH3:12])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4].Br[CH2:14][CH2:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:17]=1[Cl:29].C(N(CC)C(C)C)(C)C.O>CN(C)C=O>[Cl:29][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][C:16]=1[CH2:15][CH2:14][NH:1][C@@H:2]([CH3:12])[C@H:3]([OH:4])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6931143P-HydroxynorephedrineHCID 12049887Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate

Product 1

HCID 12049888HCID 12049888, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (1R,2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (97 mg), ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate (187 mg) and N,N-diisopropylethylamine (203 μl) in N,N-dimethylformamide (3 ml) was stirred for 10 hours at 60° C. After cooling, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo, purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=30/1) gave ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethyl]amino]ethyl]phenoxy]acetate (75 mg).

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed in vacuo, purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=30/1)

Sources & evidence

ORD record
ord-2e0b8f37b70b425cb70cc37ae43b6a59
Source dataset
uspto-grants-2002_06
Patent number
US06399660B1

Reaction notes

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