Hydrochloric Acid → Boc-Leu-(CH2)3-CH3

HRID 575865Notes

Reaction equation

HRID 575865 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH3:6].[NH:7]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:8]([C:13](N(C)OC)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11].Cl>C1(C)C=CC=CC=1.C1COCC1.C(OC(=O)C)C>[NH:7]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@H:8]([C:13]([CH2:3][CH2:4][CH2:5][CH3:6])=[O:14])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 5462224Magnesium2×HCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

Product 1

HCID 124705303Boc-Leu-(CH2)3-CH3

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Magnesium (0.330 g, 13.6 mmol) was activated by suspending in toluene for 30 min under N2. The toluene was removed and the Mg was dried under N2. To the suspension of Mg in THF (20 mL) was added bromobutane (1.46 mL, 13.6 mmol) dropwise and the mixture was heated at reflux. When all the magnesium was dissolved, Boc-Leu-N(OCH3)CH3 in THF was added dropwise and the reaction was stirred for 2 h at 0° C. 1M HCl (150 mL) was added followed by ethylacetate (100 mL). The organic layer was washed with 1M potassium hydrogen sulfate, water, dried (Na2SO4) and concentrated in vacuum. The expected product was purified by silica gel column chromatography. The product was characterized by 1H-NMR and 13C-NMR. ESI-MS: calcd. 271. found 293.3 [M+Na]+.

Workup

  1. customThe toluene was removed
  2. dry with materialthe Mg was dried under N2
  3. additionTo the suspension of Mg in THF (20 mL)
  4. temperaturethe mixture was heated
  5. temperatureat reflux
  6. washThe organic layer was washed with 1M potassium hydrogen sulfate, water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuum
  9. customThe expected product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08b15971073747d18060bca9ba57a724
Source dataset
uspto-grants-2015_05
Patent number
US09035023B2

Reaction notes

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