D-Threonine → HCID 86699926, compound

HRID 530489Notes

Reaction equation

HRID 530489 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:26])[O:15][C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>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][C:16]12[CH2:25][CH:20]3[CH2:19][CH:18]([CH2:24][CH:22]([CH2:21]3)[CH2:23]1)[CH2:17]2)=[O:26])[C:11]([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 69435D-ThreonineHCID 289319Adamantyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 86699926HCID 86699926, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottom flask, NaHCO3 (1.78 g, 21.2 mmol) was suspended in THF (4.5 mL) and H2O (9 mL), then D-threonine was added (1.0 g, 8.39 mmol). Tricyclo[3.3.1.13,7]dec-1-yl chlorocarbonate (2.0 g, 9.33 mmol) was added slowly, followed by a catalytic amount (0.1 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH of aqueous phase adjusted to 2 with 2M HCl solution. The aqueous phase was extracted four times with AcOEt, the collected organic phases were dried over Na2SO4, filtered, and the solvent removed under vacuum to give the title compound (0.250 g, 10%) as white solid. Rf=0.38 (AcOEt+1% CH3COOH, detection: ninhydrin). FTIR (cm−1): 3421, 2911, 2852, 1718, 1509, 1254, 1068.

Workup

  1. washwashed twice with Et2O and pH of aqueous phase
  2. extractionThe aqueous phase was extracted four times with AcOEt
  3. dry with materialthe collected organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-3fb73b73ce6d4ebdb8c8fca10c444d6e
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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