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

HRID 575865노트

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HRID 575865 반응식
[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]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 5462224Magnesium2회HCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-08b15971073747d18060bca9ba57a724
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035023B2

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