D-Threonine → HCID 86699966, compound

HRID 530537Notes

Reaction equation

HRID 530537 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].C([O-])(O)=O.[Na+].[C:14](=O)([O-:39])[O:15][CH:16](C1C=CC=CN=1)C1C=CC(C2C=CC(C(F)(F)F)=CC=2)=CC=1.[F:41][C:42]([F:67])([F:66])[C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52](C3C=CN(C([O-])=O)C(=O)C=3C)=[CH:51][CH:50]=2)=[CH:45][CH:44]=1>O.C1COCC1>[OH:4][C@@H:3]([CH3:5])[C@@H:2]([N:1]([C:52]1[CH:51]=[CH:50][C:49]([C:46]2[CH:45]=[CH:44][C:43]([C:42]([F:41])([F:66])[F:67])=[CH:48][CH:47]=2)=[CH:54][CH:53]=1)[C:14]([O:15][CH3:16])=[O:39])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699967HCID 86699967, compoundHCID 86699969HCID 86699969, compound

Product 1

HCID 86699966HCID 86699966, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.063 g, 0.53 mmol) and NaHCO3 (0.067 g, 0.8 mmol) in H2O (3.0 mL), the crude mixture containing 2-pyridyl-[4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.3 g, 0.8 mmol) in THF (3.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et2O (3×5 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with EtOAc (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound as transparent oil (0.21 g, quant.), which was used in the next step without further purification. MS (ESI) m/z: 415 [M−NH4]+; (ESI) m/z: 396 [M−H]−. 1H NMR (DMSO-d6): δ 1.11 (d, J=6.4 Hz, 3H), 3.97 (dd, J=3.5, 8.9 Hz, 1H), 4.05-4.12 (dq, J=3.5, 6.4 Hz, 1H), 5.13 (s, 2H), 7.00 (d, J=8.9 Hz, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.75 (d, J=8.1 Hz, 2H), 7.82 (d, J=8.1 Hz, 2H), 7.91 (d, J=8.1 Hz, 2H), 12.59 (s, 1H).

Workup

  1. additionwas added
  2. customthe crude mixture was rotary evaporated
  3. customto remove the organics and
  4. extractionsubsequently extracted with Et2O (3×5 mL)
  5. extractionsubsequently extracted with EtOAc (3×10 mL)
  6. dry with materialThe organic fraction was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8d5eb988cdb44fce894df73ce1f5e296
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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