D-Threonine → HCID 86699961, compound

HRID 530535Notes

Reaction equation

HRID 530535 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(=O)([O-])OC1C(C)=C([C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH2:28][O:29][C:25]=3[CH:24]=2)C=CN=1.[O:34]1[C:38]2C=CC(C3C=CN(C([O-])=O)C(=O)C=3C)=CC=2[O:36][CH2:35]1>O.C1COCC1>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([N:1]([C:35]([O:34][CH3:38])=[O:36])[C@H:2]([C@@H:3]([OH:4])[CH3:5])[C:6]([OH:8])=[O:7])=[CH:24][C:25]=2[O:29][CH2:28]1

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699962HCID 86699962, compoundHCID 86699964HCID 86699964, compound

Product 1

HCID 86699961HCID 86699961, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.146 g, 1.23 mmol) and NaHCO3 (0.155 g, 1.85 mmol) in H2O (3.0 mL), the crude mixture containing 1,3-benzodioxol-5-yl-methyl-2-pyridyl carbonate and 1,3-benzodioxol-5-yl-methyl-2-oxopyridine-1-carboxylate (0.506 g, 1.85 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 (0.337 g, 92%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 315 [M−NH4]+; (ESI) m/z: 296 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.4 Hz, 3H), 3.95 (dd, J=3.5, 9.0 Hz, 1H), 3.99-4.08 (dq, J=3.5, 6.4 Hz, 1H), 6.01 (s, 2H), 4.95 (s, 2H), 6.78-7.00 (m, 3H).

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-7ed191456a05448392105c2860138cc9
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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