D-Tartaric acid → (R)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (2S,3S)-2,3-dihydroxysuccinate

HRID 924300Notes

Reaction equation

HRID 924300 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH2:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[OH:27][C@@H:28]([C@H:32]([OH:36])[C:33]([OH:35])=[O:34])[C:29]([OH:31])=[O:30]>CO>[OH:27][C@@H:28]([C@H:32]([OH:36])[C:33]([OH:35])=[O:34])[C:29]([OH:31])=[O:30].[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([NH2:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 904118321-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine

Product 1

HCID 131732840(R)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (2S,3S)-2,3-dihydroxysuccinateYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To 1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (CB58) (0.60 g, 1.7 mmol) in methanol (10 mL) was added (2S,3S)-2,3-dihydroxysuccinic acid (0.25 g, 1.7 mmol). The resultant solid was filtered and air dried overnight: mp 182-185° C. The solid was redissolved in methanol (10 mL) and heated to reflux (˜65° C.). The solution was cooled to room temperature and let stand overnight. The white solid that formed was filtered and air-dried to give the title compound as a white solid (0.40 g, 46%): mp 191-194° C.; 1H NMR (400 MHz, CDOD3) d 9.16 (s, 1H), 8.15 (d, J=8.2 Hz, 2H), 8.02 (d, J=9.1 Hz, 2H), 7.50 (dd, J=9.2, 1.0 Hz, 2H), 7.41 (d, J=8.2 Hz, 2H), 4.40 (s, 2H), 3.59 (dt, J=8.1, 6.2 Hz, 1H), 3.07 (dd, J=13.6, 6.1 Hz, 1H), 2.88 (dd, J=13.6, 8.3 Hz, 1H), 1.29 (d, J=6.5 Hz, 3H) (OH and NH2 not observed).

Workup

  1. filtrationThe resultant solid was filtered
  2. customair dried overnight
  3. dissolutionThe solid was redissolved in methanol (10 mL)
  4. temperatureheated
  5. temperatureThe solution was cooled to room temperature
  6. customThe white solid that formed
  7. filtrationwas filtered
  8. customair-dried

Sources & evidence

ORD record
ord-bf5265f55ea5407eba7d786a4506641f
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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