D-Threonine → HCID 86699945, compound

HRID 530519Notes

Reaction equation

HRID 530519 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(CCOCCC2C=CC=CC=2)=CC=CN=1.[CH2:35]([O:43][CH2:44][CH2:45][O:46][C:47](N1C=CC=CC1=O)=[O:48])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O.C1COCC1>[OH:4][C@@H:3]([CH3:5])[C@@H:2]([NH:1][C:47]([O:46][CH2:45][CH2:44][O:43][CH2:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:48])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 73294494HCID 73294494, compoundHCID 86699946HCID 86699946, compound

Product 1

HCID 86699945HCID 86699945, compoundYield 97.6%

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, 1.25 mmol) in H2O (3.0 mL), the crude isomeric mixture containing 2-phenethyloxyethyl-2-pyridyl carbonate and 2-phenethyloxyethyl-2-oxopyridine-1-carboxylate (0.54 g, 1.89 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 (0.38 g, 94%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 312 [M−H]+; (ESI) m/z: 310 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.4 Hz, 3H), 2.81 (t, J=7.1 Hz, 2H), 3.55-3.66 (m, 4H), 3.93 (dd, J=3.4, 8.9 Hz, 1H), 4.00-4.15 (m, 3H), 6.83 (d, J=8.9 Hz, 1H), 7.14-7.32 (m, 5H), 12.20 (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-bdad8d7c49cc47499aba7b30c3cfeedd
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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