D-Threonine → HCID 86699914, compound

HRID 530478Notes

Reaction equation

HRID 530478 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@@H](C)CCCCCCC)=CC=CN=1.[CH3:33][C@H:34]([O:42][C:43](N1C=CC=CC1=O)=[O:44])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>O.C1COCC1>[OH:4][C@@H:3]([CH3:5])[C@@H:2]([NH:1][C:43]([O:42][C@@H:34]([CH3:33])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:44])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699915HCID 86699915, compoundHCID 86699917HCID 86699917, compound

Product 1

HCID 86699914HCID 86699914, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of D-threonine (0.150 g, 1.25 mmol) and NaHCO3 (0.158 g, 1.89 mmol) in water (3 mL), the crude mixture containing [(1S)-1-methyloctyl]-2-pyridyl carbonate and [(1S)-1-methyloctyl]-2-oxopyridine 1-carboxylate (0.501 g, 1.88 mmol) in THF (3 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 (0.220 g, 62%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 290 [M−H]+; (ESI) m/z: 288 [M−H]−. 1H NMR (DMSO-d6): δ 0.87 (t, J=6.8 Hz, 3H), 1.09 (d, J=6.4 Hz, 3H), 1.15 (d, J=6.2 Hz, 3H), 1.21-1.34 (m, 10H), 1.40-1.57 (m, 2H), 3.92 (dd, J=3.4, 9.0 Hz, 1H), 4.01-4.11 (m, 1H), 4.60-4.70 (m, 1H), 6.55 (d, J=9.0 Hz, 1H), 12.49 (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-92a3c604c4e54686ace67d6ebc6d70e8
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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