Sodium Carbonate → HCID 88182969, compound

HRID 2185583Notes

Reaction equation

HRID 2185583 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:13])[C@H:7]([C@H:9]([CH2:11][CH3:12])[CH3:10])[NH2:8])([CH3:4])[CH3:3].Br[CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>CN1C(=O)N(C)CCC1.O>[CH3:4][C:2]([O:5][C:6](=[O:13])[C@H:7]([C@H:9]([CH2:11][CH3:12])[CH3:10])[N:8]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 10340Sodium Carbonate2×HCID 79177tert-Butyl bromoacetate2×HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 701053916874-08-1

Product 1

HCID 88182969HCID 88182969, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
90 °C

Procedure

L-isoleucine 1,1-dimethylethylester (23.00 g; 122.8 mmol), (2-Bromoethoxy)-(1,1-dimethylethyl)dimethylsilane (30.26 g, 126.5 mmol) and Na2CO3 (26.18 g; 247.0 mmol) were stirred in DMPU (Aldrich art. 25,156-9) (300 mL) at 90° C. for 20 h. The intermediate product was not isolated, but after cooling the mixture to roughly 40° C., tert-butyl bromoacetate (commercial product) (19.0 mL; 130 mmol) and further Na2CO3 (27.00 g; 254.7 mmol) were added, then heating at 90° C. was restored. More tert-butyl bromoacetate (2.0 mL; 14 mmol) was added after 4 h and heating prolonged for another 2 h. The mixture was cooled to 0° C., then water (600 mL) was cautiously added (exothermic solubilization). Once clear, the solution was extracted with diethyl ether (4×250 mL); the combined organic layers were washed with water (3×250 mL), brine (250 mL), at last dried over Na2SO4. After removal of solvents in vacuo, the residual oil was purified by flash chromatography (n-hexane/iPr2O 95:5). The desired compound was obtained (42.25 g; 91.90 mmol). Yield 75%.

Workup

  1. customThe intermediate product was not isolated
  2. temperatureafter cooling the mixture to roughly 40° C.
  3. temperatureheating
  4. temperatureThe mixture was cooled to 0° C.
  5. extractionOnce clear, the solution was extracted with diethyl ether (4×250 mL)
  6. washthe combined organic layers were washed with water (3×250 mL), brine (250 mL)
  7. dry with materialat last dried over Na2SO4
  8. customAfter removal of solvents in vacuo
  9. customthe residual oil was purified by flash chromatography (n-hexane/iPr2O 95:5)

Sources & evidence

ORD record
ord-ea2bb1dcc49c420aac925975d03eaf6d
Source dataset
uspto-grants-2002_06
Patent number
US06403055B1

Reaction notes

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