D-Threonine → HCID 86699971, compound

HRID 530539Notes

Reaction equation

HRID 530539 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-:34])[O:15][CH:16](C1C=CC=CN=1)C1C=CC(C2C=CSC=2)=CC=1.[S:36]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44](C3C=CN(C([O-])=O)C(=O)C=3C)=[CH:43][CH:42]=2)=[CH:37]1>O.C1COCC1>[OH:4][C@@H:3]([CH3:5])[C@@H:2]([N:1]([C:44]1[CH:43]=[CH:42][C:41]([C:38]2[CH:39]=[CH:40][S:36][CH:37]=2)=[CH:46][CH:45]=1)[C:14]([O:15][CH3:16])=[O:34])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699972HCID 86699972, compoundHCID 86699974HCID 86699974, compound

Product 1

HCID 86699971HCID 86699971, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.067 g, 0.56 mmol) and NaHCO3 (0.07 g, 0.84 mmol) in H2O (3.0 mL), the crude mixture containing 2-pyridyl-[4-(3-thienyl)-phenyl]-methyl carbonate and [4-(3-thienyl)-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.263 g, 0.84 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 (0.188 g, quant.) as white solid, which was used in the next step without further purification. MS (ESI) m/z: 353 [M−NH4]+. 1H NMR (DMSO-d6) δ: 1.10 (d, J=6.4 Hz, 3H), 3.97 (dd, J=3.5, 8.9 Hz, 1H), 4.08 (dq, J=3.5, 6.4 Hz, 1H), 5.07 (s, 2H), 6.96 (d, J=8.9 Hz, 1H), 7.41 (d, J=8.1 Hz, 2H), 7.53-7.60 (m, 1H), 7.64 (dd, J=2.9, 5.0 Hz, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.86-7.91 (m, 1H), 12.58 (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-e5e3b1e167aa419a913a5c4616e62c74
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

Loading…