Hydrochloric Acid → HCID 12809805, compound

HRID 345902Notes

Reaction equation

HRID 345902 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20].[C:25]([NH:32][C@H:33]([CH:38]=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].Cl>O1CCCC1>[CH2:23]([O:22][C:19](=[O:21])[CH2:20][CH:38]([OH:39])[CH:33]([NH:32][C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH3:24]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8058HexaneHCID 8857Ethyl AcetateHCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178418339Butyllithium

Product 1

HCID 12809805HCID 12809805, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To diisopropylamine (7.7 g, 0.077 mol) in dry tetrahydrofuran (26 mL) cooled to -20 degrees C. under argon was added dropwise n-butyllithium in hexane (1.46 M, 52.4 mL, 0.077 mol). The solution was stirred 15 min, the temperature lowered to -78 degrees C. and dry ethyl acetate (6.7 g, 0.077 mol) added dropwise while maintaining the temperature below -75 degrees C. The solution was stirred 10 min and a precooled (-78 degrees C.) tetrahydrofuran solution of Boc-L-leucinal (11 g, 0.051 mol) was added. After 30 min, 2 M HCl (40 mL) was added and the mixture was slowly warmed to 10 degrees C. and extracted with ether (3 ×200 mL). The combined ethereal extract was washed with saturated sodium chloride and dried with magnesium sulfate and filtered. Evaporation of the filtrate in vacuo gave 14 g of crude product which was purified by flash chromatography (20% ethyl acetate in hexane) to give 6 g of desired product.

Workup

  1. customlowered to -78 degrees C
  2. temperaturewhile maintaining the temperature below -75 degrees C
  3. stirringThe solution was stirred 10 min
  4. waitAfter 30 min
  5. extractionand extracted with ether (3 ×200 mL)
  6. extractionThe combined ethereal extract
  7. washwas washed with saturated sodium chloride
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. customEvaporation of the filtrate in vacuo
  11. customgave 14 g of crude product which
  12. customwas purified by flash chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-24d0b1c8b43b4fb48a3979d224182f15
Source dataset
uspto-grants-1991_10
Patent number
US05059589

Reaction notes

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