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Chemical Structure| 199005-69-1 Chemical Structure| 199005-69-1

Structure of 199005-69-1

Chemical Structure| 199005-69-1

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Product Details of [ 199005-69-1 ]

CAS No. :199005-69-1
Formula : C16H24N2O5
M.W : 324.37
SMILES Code : CC(C)(C)OC(NC[C@@H](CO)NC(OCC1=CC=CC=C1)=O)=O
MDL No. :MFCD06796908

Safety of [ 199005-69-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 199005-69-1 ]

* 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 [ 199005-69-1 ]

[ 199005-69-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 16947-84-5 ]
  • [ 199005-69-1 ]
YieldReaction ConditionsOperation in experiment
78% To a solution of <strong>[16947-84-5](S)-2-(((benzyloxy)carbonyl)amino)-3-((t-butoxycarbonyl)amino)propanoic acid</strong> (900 mg, 2.66 mmol) in DME (10 mL) at -15° C. were successively added a solution of N-methyl morpholine (0.33 mL, 3 mmol) and isobutyl chloroformate (0.35 mL, 2.66 mmol).The reaction was stirred at -15 to -10° C. for 15 minutes.The precipitated N-methyl morpholine HCl was removed by filtration and washed with DME (10 mL), the combine filtrates were chilled to -15° C. in an ice-salt bath.Then a solution of sodium borohydride (301 mg, 7.98 mmol) in water (5 mL) was added in one portion at -15° C.This reaction mixture was stirred at this temperature for 10 minutes. The reaction was quenched by the addition of saturated aqueous NH4Cl and the resulting mixture was extracted with ethyl acetate.The organic layer was washed with brine and dried over sodium sulfate.The solution was then filtered and concentrated in vacuo, purified on column (0-70percent ethyl acetate/hexane) to give product as a white powder (675 mg, 78percent);1H NMR (CDCl3) (400 MHz) (MeOD) delta 7.34 (m, 5H), 5.09 (s, 2H), 3.73 (m, 1H), 3.24 (m, 4H), 1.44 (s, 9H);13C NMR delta 158.6, 138.3, 129.5, 129.0, 128.9, 80.3, 67.5, 63.0, 54.6, 42.1, 28.8.
78% To a solution of ()-2-(((benzyloxy)carbonyl)amino)-3 -((tbutoxycarbonyl)amino)propanoic acid (900 mg, 2.66 mmol) in DME (10 mL) at -15 °C were successively added a solution of N-methyl morpholine (0.33 mL, 3 mmol) and isobutylchloroformate (0.35 mL, 2.66 mmol). The reaction was stirred at -15 to -10 °C for 15 minutes.The precipitated N-methyl morpholine HC1 was removed by filtration and washed with DME(10 mL), the combine filtrates were chilled to -15 °C in an ice-salt bath. Then a solution ofsodium borohydride (301 mg, 7.98 mmol) in water (5 mL) was added in one portion at -15 °C. This reaction mixture was stirred at this temperature for 10 minutes. The reaction was quenched by the addition of saturated aqueous NH4C1 and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solution was then filtered and concentrated under reduced pressure, purified by column chromatographyon silica gel (0- 70percent ethyl acetate hexane) to give product as a white powder (675 mg, 78percent yield); ?HNMR (400 MHz) (CD3OD) 7.34 (m, 5H), 5.09 (s, 2H), 3.73 (m, 1H), 3.24 (m, 4H), 1.44 (s, 9H); ?3C NMR (100 MHz, CD3OD) 158.6, 138.3, 129.5, 129.0, 128.9, 80.3, 67.5,63.0, 54.6, 42.1, 28.8.
78% To a solution of (S)-2-(((benzyloxy)carbonyl)amino)-3-((t- butoxycarbonyl)amino)propanoic acid (900 mg, 2.66 mmol) in DME (10 mL) at -15 oC were successively added a solution of N-methyl morpholine (0.33 mL, 3 mmol) and isobutyl chloroformate (0.35 mL, 2.66 mmol). The reaction was stirred at -15 to -10 oC for 15 minutes. The precipitated N-methyl morpholine HCl was removed by filtration and washed with DME (10 mL), the combine filtrates were chilled to -15 oC in an ice-salt bath. Then a solution of sodium borohydride (301 mg, 7.98 mmol) in water (5 mL) was added in one portion at -15 oC. This reaction mixture was stirred at this temperature for 10 minutes. The reaction was quenched by the addition of saturated aqueous NH4Cl and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solution was then filtered. concentrated under reduced pressure and purified by column chromatography on silica gel (0- 70 percent ethyl acetate/ hexanes) to give product as a white powder (675 mg, 78 percent yield); 1H NMR (400 MHz) (CD3OD) delta 7.34 (m, 5H), 5.09 (s, 2H), 3.73 (m, 1H), 3.24 (m, 4H), 1.44 (s, 9H); 13C NMR (100 MHz, CD3OD) delta 158.6, 138.3, 129.5, 129.0, 128.9, 80.3, 67.5, 63.0, 54.6, 42.1, 28.8.
72% A round bottom flask was charged with (S)-4L1 (15.90 g,47.0 mmol),14a and 1,2-dimethoxyethane (65 mL), and N-methylmorpholine (5.4 mL; 5.0 g, 49 mmol) were added with stirring.The solution was cooled to 25 C, and isobutyl chloroformate(6.50 mL; 6.8 g, 50 mmol) was slowly added. The cold bath wasthen removed. After 30 min, the precipitate was collected byfiltration and washed with 1,2-dimethoxyethane (2 30 mL). Thecombined filtrate and washings were sparged with nitrogen andcooled to 0 C. A solution of NaBH4 (2.52 g, 66.5 mmol) in EtOH(150 mL) was then added dropwise with stirring. After 1 h, H2O(10 mL) was cautiously added, after which the cold bath wasremoved. After 12 h, the solvent was removed by rotaryevaporation. The solid was dissolved in EtOAc (200 mL), and H2O(200 mL) was added. The aqueous phase was extracted withEtOAc (2 50 mL) and the combined organic phases were dried(MgSO4). The solvent was removed by rotary evaporation and thesolid was chromatographed on a silica gel column (4 17 cm,20:80 to 50:50 v/v EtOAc/hexane). The solvent was removedfrom the product containing fraction by rotary evaporation. Theresidue was dried by oil pump vacuum to give (S)-5L1 (11.0 g,33.8 mmol, 72percent) as a white solid
Benzyl t-butyl (3-hydroxypropane-1,2-diyl)(S)-dicarbamate To a solution of <strong>[16947-84-5](S)-2-(((benzyloxy)carbonyl)amino)-3-((t-butoxycarbonyl)amino)propanoic acid</strong> (900 mg, 2.66 mmol) in DME (10 mL) at -15° C. were successively added a solution of N-methyl morpholine (0.33 mL, 3 mmol) and isobutyl chloroformate (0.35 mL, 2.66 mmol). The reaction was stirred at -15° C. to -10° C. for 15 minutes. The precipitated N-methyl morpholine HCl was removed by filtration and washed with DME (10 mL), the combine filtrates were chilled to -15° C. in an ice-salt bath. Then a solution of sodium borohydride (301 mg, 7.98 mmol) in water (5 mL) was added in one portion at -15° C. This reaction mixture was stirred at this temperature for 10 minutes. The reaction was quenched by the addition of saturated aq. NH4Cl and the resulting mixture was extracted with Ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solution was then filtered and concentrated in vacuo, purified on column (0-70 Ethyl acetate/hexane) to give product as a white powder (675 mg, 78percent); 1H NMR (400 MHz) (MeOD) delta 7.34 (m, 5H), 5.09 (s, 2H), 3.73 (m, 1H), 3.24 (m, 4H), 1.44 (s, 9H); 13C NMR delta 158.6, 138.3, 129.5, 129.0, 128.9, 80.3, 67.5, 63.0, 54.6, 42.1, 28.8.

 

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