D-Threonine → HCID 57523548, compound

HRID 530476Notes

Reaction equation

HRID 530476 reaction equation
C([O-])(O)=O.[Na+].[NH2:6][C@@H:7]([C:11]([OH:13])=[O:12])[C@H:8]([CH3:10])[OH:9].[C:14](Cl)(=[O:27])[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:9][C@@H:8]([CH3:10])[C@@H:7]([NH:6][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:27])[C:11]([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 69435D-ThreonineHCID 516892Sodium BicarbonateHCID 86699913HCID 86699913, compound

Product 1

HCID 57523548HCID 57523548, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottom flask, NaHCO3 (12.0 g, 143.2 mmol) was suspended in THF (30 mL) and water (60 mL), then D-threonine (6.8 g, 56.8 mmol) was added followed by 5-phenylpentyl chlorocarbonate (14.3 g, 63.1 mmol) and a catalytic amount (0.67 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (4×150 mL), the collected organic phases were washed with brine, dried over Na2SO4, filtered and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (20:80+1% CH3COOH), yielding the title compound (3.15 g, 18%), as pale yellow oil. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3332 (br), 3027, 2935, 2859, 1714, 1530, 1454, 1415, 1257, 1072, 1007, 963, 870, 779, 748, 700. 1H NMR (CDCl3): δ 1.26 (d, 3H); 1.39 (m, 2H); 1.62-1.68 (m, 4H); 2.61 (t, 2H); 4.08 (t, 2H); 4.34 (d, 1H); 4.42 (d, 1H); 5.68 (d, 1H); 7.16-7.78 (m, 3H); 7.26-7.28 (m, 2H).

Workup

  1. washwashed twice with Et2O
  2. extractionThe aqueous phase was extracted with AcOEt (4×150 mL)
  3. washthe collected organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customThe crude was purified by typical silica gel column chromatography
  8. washeluting with Cy/AcOEt (20:80+1% CH3COOH)

Sources & evidence

ORD record
ord-647e7ed5448841a8bb9b14f91f67b340
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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