D-Threonine → HCID 86699907, compound

HRID 530464Notes

Reaction equation

HRID 530464 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].Cl[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:16]>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:9][C@@H:8]([CH3:10])[C@@H:7]([NH:6][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:16])[C:11]([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 69435D-ThreonineHCID 69489Pentyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 86699907HCID 86699907, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottom flask NaHCO3 (13.0 g, 155.3 mmol) was suspended in THF (35 mL) and water (70 mL), then D-threonine (7.33 g, 61.6 mmol) and tetrabutylamonium bromide (0.733 g) were added. Amyl chloroformate (10 mL, 68.4 mmol) was added dropwise and the reaction vigorously stirred 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, the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to yield the tile compound (13.0 g, 90%) as pale yellow oil, which was used in the next step without further purification. Rf=0.26 (Cy/AcOEt 2:8+1% CH3COOH; detection: ninhydrin, bromocresol green). FTIR (cm−1): 3344, 2959, 2932, 2873, 1724, 1529, 1468, 1415 1378, 1258, 1075.

Workup

  1. customthe reaction vigorously stirred 18 h at rt
  2. washwashed twice with Et2O
  3. extractionThe aqueous phase was extracted with AcOEt
  4. dry with materialthe collected organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-dae247a64c444b90b2d2c898b27376a7
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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