D-Threonine → HCID 86699976, compound

HRID 530542Notes

Reaction equation

HRID 530542 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-:35])[O:15][C:16]1C(C)=C(C2C=CC(C3CCCCC3)=CC=2)C=CN=1.[CH:37]1([O:43][C:44]2[CH:49]=[CH:48][C:47](C3C=CN(C([O-])=O)C(=O)C=3C)=[CH:46][CH:45]=2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>O.C1COCC1>[CH:37]1([O:43][C:44]2[CH:49]=[CH:48][C:47]([N:1]([C:14]([O:15][CH3:16])=[O:35])[C@H:2]([C@@H:3]([OH:4])[CH3:5])[C:6]([OH:8])=[O:7])=[CH:46][CH:45]=2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699957HCID 86699957, compoundHCID 86699977HCID 86699977, compound

Product 1

HCID 86699976HCID 86699976, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.08 g, 0.67 mmol) and NaHCO3 (0.084 g, 1.0 mmol) in H2O (3.0 mL), the crude mixture containing (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and [4-(cyclohexoxy)-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.327 g, 1.0 mmol) in THF (3.0 mL) was added. After 15 h at r.t., 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 (0.214 g, 91%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 369 [M−NH4]+; (ESI) m/z: 350 [M−H]−. 1H NMR (DMSO-d6): δ 1.08 (d, J=6.3 Hz, 3H), 1.21-1.48 (m, 5H), 1.48-1.57 (m, 1H), 1.66-1.74 (m, 2H), 1.87-1.95 (m, 2H), 3.95 (dd, J=3.4, 9.0 Hz, 1H), 4.06 (dq, J=3.4, 6.3 Hz, 1H), 4.29-4.36 (m, 1H), 6.84 (d, J=9.0 Hz, 1H), 6.91 (d, J=8.3 Hz, 2H), 7.27 (d, J=8.3 Hz, 2H).

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-bc5f8304920748f9a14aaefb9d0e07ee
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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