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Chemical Structure| 101214-43-1 Chemical Structure| 101214-43-1

Structure of Fmoc-Phe-OSu
CAS No.: 101214-43-1

Chemical Structure| 101214-43-1

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Product Details of [ 101214-43-1 ]

CAS No. :101214-43-1
Formula : C28H24N2O6
M.W : 484.50
SMILES Code : O=C1CCC(N1OC([C@H](CC2=CC=CC=C2)NC(OCC3C4=CC=CC=C4C5=CC=CC=C53)=O)=O)=O
English Name :2,5-Dioxopyrrolidin-1-yl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate
MDL No. :MFCD00062204
InChI Key :VLXHZQQUTCVLGU-DEOSSOPVSA-N
Pubchem ID :11826988

Safety of [ 101214-43-1 ]

Application In Synthesis of [ 101214-43-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 101214-43-1 ]

[ 101214-43-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 101214-43-1 ]
  • [ 147-85-3 ]
  • [ 138372-76-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;
  • 2
  • [ 101214-43-1 ]
  • [ 756487-18-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane 2: di-tert-butyl dicarbonate; pyridine / dimethylformamide 3: Et2NH / CH2Cl2 4: i-Pr2NEt / CH2Cl2
  • 3
  • [ 101214-43-1 ]
  • [ 206133-42-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane 2: di-tert-butyl dicarbonate; pyridine / dimethylformamide
  • 4
  • [ 1187-84-4 ]
  • [ 101214-43-1 ]
  • [ 1359015-18-1 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: S-methyl-L-cysteine; Fmoc-Phe-ONSu With potassium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate
  • 5
  • [ 28798-28-9 ]
  • [ 101214-43-1 ]
  • [ 2232212-09-6 ]
YieldReaction ConditionsOperation in experiment
325 mg With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h; Fmoc-Phe-L-Cys(Acm)-OH (35) Fmoc-Phe-L-Cys(Acm)-OH (35). N,N′-Dicyclohexylcarbodiimide (268 mg, 1.3 mmol, 1.0 equiv.) and NHS (156 mg, 1.4 mmol, 1.1 equiv.) were added sequentially to a solution of Fmoc-Phe-OH (33) (501 mg, 1.3 mmol, 1 equiv.) in CH2Cl2 (10 mL) at 0 C under N2 and stirred for 30 min. The mixture was warmed to rt and stirred for 3 h, filtered, concentrated to 5 mL, and left in the freezer for 21 h. The urea precipitate was removed by filtration again and the filtrate concentrated. The residue was taken up in DMF (4 mL) and HCl·H-L-Cys(Acm)-OH (34) (235 mg, 1.0 mmol, 1.0 equiv.) was added, followed by diisopropylethylamine (270 μL, 194 mg, 1.5 mmol, 1.5 equiv.) dropwise. The mixture was stirred at rt for 18 h, diluted with EtOAc (100 mL) and washed with water (100 mL), 10% aq. citric acid (100 mL) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 0-10% MeOH in CH2Cl2 to afford Fmoc-Phe-L-Cys(Acm)-OH (35) as a colorless powder (325 mg, 57%) that was carried into the next step without further purification. Rf 0.05 (9:1 CH2Cl2-MeOH).
  • 6
  • [ 2310209-66-4 ]
  • [ 101214-43-1 ]
  • [ 206133-42-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; 1 To a solution of compound 4 (1.80 g, 5.12 mmol) and compound 5 (2.36 g, 4.87 mmol) in DMF (60 mL) was added DIEA (993 mg, 7.68 mmol, 1.34 mL). The mixture was stirred at 20 °C for 4 hrs. LC-MS showed 64.0% of desired compound (Rt = 2.020 min) was detected. The reaction mixture was concentrated under reduced pressure to give a residue which was triturated with CH3CN (50 mL) and MTBE (50 mL). Compound 6 (2.53 g, 63.8% yield, 93.2% purity) was obtained as a white solid.
 

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