Ammonium → (S)-2-Amino-3-[4-(tert-butoxy)phenyl]propanamide

HRID 895161

반응식

HRID 895161 반응식
C([NH:18][C@H:19]([C:32]([OH:34])=O)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH4+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[N:51]1C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.ClCCl.C(NCC)C>[C:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@@H:19]([C:32]([NH2:51])=[O:34])[NH2:18])=[CH:22][CH:23]=1)([CH3:31])([CH3:30])[CH3:29]

참가 물질

9

반응물 4

HCID 223AmmoniumHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 10895791Fmoc-L-Tyr(tBu)-OH

생성물 1

HCID 15024317(S)-2-Amino-3-[4-(tert-butoxy)phenyl]propanamide수율 81%

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 8021Diethylamine용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

N-Fmoc-O-tert-butyl-tyrosine (3.27 g, 7.12 mmol) was dissolved in dioxane (15 mL). Ammonium hydrogenocarbonate (732 mg, 9.26 mmol), di-tert-butyl-dicarbonate (2.02 g, 9.26 mmol) and pyridine (0.4 mL) were added and the mixture was stirred under nitrogen atmosphere at room temperature for 12 h. It was then diluted with ethyl acetate and the organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again. It was dried over magnesium sulfate and concentrated. The crude thus obtained (3.17 g) was dissolved in dichloromethane (50 mL) and diethylamine (10 mL). The mixture was stirred at room temperature for 12 h, concentrated under reduced pressure and purified by flash chromatography with DCM/MeOH/NH4OH (95/5/1 then 90/10/1) to give 1.37 g of the desired compound (yield=81%).

후처리

  1. washthe organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again
  2. dry with materialIt was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude thus obtained (3.17 g)
  5. stirringThe mixture was stirred at room temperature for 12 h
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography with DCM/MeOH/NH4OH (95/5/1

출처 및 근거

ORD 기록
ord-b15450ccefdb4851b3300913d415f364
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914069B2

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