D-Threonine → HCID 73291991, compound

HRID 530515Notes

Reaction equation

HRID 530515 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:27]C1C=CC=CN=1)[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.O=C1C=CC=CN1C(OCCCCCC1CCCCC1)=O>O.C1COCC1>[CH:21]1([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]([NH:1][C@H:2]([C@@H:3]([OH:4])[CH3:5])[C:6]([OH:8])=[O:7])=[O:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699943HCID 86699943, compoundHCID 86699944HCID 86699944, compound

Product 1

HCID 73291991HCID 73291991, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.15 g, 1.25 mmol) and NaHCO3 (0.16 g, 1.89 mmol) in H2O (3.5 mL), the crude mixture containing 5-cyclohexylpentyl 2-pyridyl carbonate and 5-cyclohexylpentyl 2-oxopyridine 1-carboxylate (0.55 g, 1.5 mmol) in THF (3.5 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 2M HCl solution to pH 2-3 and subsequently extracted with AcOEt (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.32 g, 81%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 316 [M−H]+; (ESI) m/z: 314 [M−H]−. 1H NMR (DMSO-d6): δ 0.77-0.93 (m, 2H), 1.02-1.37 (m, 13H), 1.45-1.72 (m, 7H), 3.88-3.99 (m, 3H), 4.01-4.11 (m, 1H), 6.66 (d, J=9.0 Hz, 1H), 11.77 (br 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 AcOEt (3×10 mL)
  6. dry with materialThe organic fraction was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f0eba303a48940de93932c61f806cfc1
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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