Dimethylacetamide → HCID 13424839, compound

HRID 274991Notes

Reaction equation

HRID 274991 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]([OH:30])[CH:13]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH2:28][CH3:29])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.CC([N:35](C)C)=O>N>[NH2:35][CH2:11][CH:12]([OH:30])[CH:13]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH3:29])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 13479314HCID 13479314, compound

Product 1

HCID 13424839HCID 13424839, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of (RS,SR)-1-(p-toluenesulfonyloxy)-2-hydroxy-3-(2-ethoxy-phenoxy)-3-phenyl-propane (4.3 g) in dimethylacetamide (125 ml), 30% aqueous ammonia (125 ml) was added and the reaction mixture was kept for 12 hours at room temperature in an hermetically sealed vessel. The mixture was then concentrated under vacuum to a small volume, poured into water, saturated with NaCl, and extracted with ethylacetate. The organic phase was washed with water, dried over Na2SO4, filtered, and the solvent evaporated under vacuum. The obtained oily residue was purified on chromatographic column (CHCl3 :CH3OH:NH4OH 180:20:2 as eluant), to give 1,1 g of 1-amino-2-hydroxy-3-(2-ethoxy-phenoxy)-3-phenyl-propane as single RS,SR diastereoisomer, m.p. 115°-117° C. In analogous fashion, using appropriate starting compounds prepared according to the procedure described in the example 1, 2 and 7, the compound 1-amino-2-hydroxy-3-(4-trifluoromethyl-phenoxy)-3-phenyl-propane was obtained as single RS,SR diastereoisomer, m.p. 120°-122° C.

Workup

  1. concentrationThe mixture was then concentrated under vacuum to a small volume
  2. additionpoured into water, saturated with NaCl
  3. extractionextracted with ethylacetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customThe obtained oily residue was purified on chromatographic column (CHCl3 :CH3OH:NH4OH 180:20:2 as eluant)

Sources & evidence

ORD record
ord-2f5020fb807b43d68ff589f6cc12a1fd
Source dataset
uspto-grants-1995_02
Patent number
US05391735

Reaction notes

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