(-)-Mandelic acid → HCID 66705909, compound

HRID 2276378Notes

Reaction equation

HRID 2276378 reaction equation
[NH2:1][C@@H:2]([CH2:5][O:6][C@H:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH3:8])[CH2:3][OH:4].N[C@H](CO[C@H](C1C=CC(F)=CC=1)C)CO.[C:31](O)(=[O:40])[C@@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[OH:33]>C(O)(C)C>[OH:33][C@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:31]([O:4][CH2:3][C@H:2]([NH2:1])[CH2:5][O:6][C@H:7]([C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)[CH3:8])=[O:40]

Participants

5

Reactant 3

HCID 11914(-)-Mandelic acidHCID 66705889HCID 66705889, compoundHCID 66705965HCID 66705965, compound

Product 1

HCID 66705909HCID 66705909, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a stirred solution of the 80:20 mixture of (R)-2-amino-3-[(S)-1-(4-fluoro-phenyl)-ethoxy]-propan-1-ol & (S)-2-amino-3-[(S)-1-(4-fluoro-phenyl)-ethoxy]-propan-1-ol (2.94 g) in isopropanol (3 ml) was added a solution of D-(−)-mandelic acid (2.10 g) in isopropanol (2 ml). The solvent was evaporated and replaced with ethyl acetate to afford white crystals which were collected by filtration. The crystals were dissolved in hot EtOAc (65 ml) at 80° C. and the mixture was allowed to cool slowly. Crystals appeared on reaching a temperature of 70° C. and the suspension was then stirred at room temperature for 16 h. The crystals were collected by filtration and redissolved in hot EtOAc (80 ml) at 80° C. and the mixture was allowed to cool slowly until cyrstallisation started and then the resulting suspension was stirred at room temperature for 16 h. The crystals were collected by filtration to afford pure (R)-2-amino-3-[(S)-1-(4-fluoro-phenyl)-ethoxy]-propan-1-ol (R)-hydroxy-phenyl-acetate (3.08 g, 61%) as a white solid. 1H NMR (300 MHz, DMSO, δ ppm): 1.34 (d, J=6.3 Hz, 3H), 3.13 (m, 1H), 3.23 (m, 1H), 3.37 (m, 4H), 3.83 (m, 1H), 4.46 (q, J=6.3 Hz, 1H), 4.54 (s, 1H), 7.20 (m, 5H), 7.35 (m, 4H).

Workup

  1. customThe solvent was evaporated
  2. customto afford white crystals which
  3. filtrationwere collected by filtration
  4. dissolutionThe crystals were dissolved in hot EtOAc (65 ml) at 80° C.
  5. temperatureto cool slowly
  6. customa temperature of 70° C.
  7. filtrationThe crystals were collected by filtration
  8. dissolutionredissolved in hot EtOAc (80 ml) at 80° C.
  9. temperatureto cool slowly until cyrstallisation
  10. stirringthe resulting suspension was stirred at room temperature for 16 h
  11. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-0287e7fedb2d4c98aa74b3a27934db7f
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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