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CAS No. : | 3303-55-7 | MDL No. : | MFCD00038297 |
Formula : | C15H22N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RFCVXVPWSPOMFJ-STQMWFEESA-N |
M.W : | 278.35 | Pubchem ID : | 76808 |
Synonyms : |
H-Phe-Leu-OH
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium tetrahydroborate In acetone Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Leu-Sasrin resin In tetrahydrofuran; dichloromethane efffect of temp. and reagents (as imidazole, N-hydroxybenztriazole); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In dichloromethane; water at 0℃; for 5.5h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium tetrahydroborate In acetone for 1.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1-methyl-piperazine; potassium carbonate In water; N,N-dimethyl-formamide; acetonitrile for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium carbonate In tetrahydrofuran; water for 24h; Ambient temperature; pH 9-9.2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide at 4℃; for 48h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In water; acetic acid; <i>tert</i>-butyl alcohol Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; acetic acid; isopropyl alcohol Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.4% | With sulfuric acid In 1,4-dioxane at 25℃; for 5.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With triethylamine In water; acetonitrile at 40℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride for 4h; Heating; | |
94% | With hydrogenchloride at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With 4-methyl-morpholine; triethylamine; isobutyl chloroformate In tetrahydrofuran; N,N-dimethyl-formamide -5 deg C, 30 min; rt, 24 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sulfuryl dichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With trimethylaluminum In 1,2-dichloro-ethane at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With trimethylaluminum In 1,2-dichloro-ethane at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethylaluminum In hexane; 1,2-dichloro-ethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With trimethylaluminum In hexane; 1,2-dichloro-ethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trimethylaluminum In hexane; 1,2-dichloro-ethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With trimethylaluminum In hexane; 1,2-dichloro-ethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With trimethylaluminum In hexane; 1,2-dichloro-ethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; polymer-bound 4-hydroxy-3-nitrobenzophenone,DCC; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide 1.) CH2Cl2, THF, 1 H, 25 deg C, -10 -0 deg C,10 h; 2.) 0 deg C, CH2Cl2, 24 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With trifluoroacetic acid In dichloromethane at 0℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; palladium Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; platinum Hydrogenation.Erwaermen des Reaktionsprodukts mit wss. Aethanol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; palladium; acetic acid Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hydroxide; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 160 - 170℃; | ||
Multi-step reaction with 2 steps 1: 94 percent / HCl / 12 h / 20 °C 2: 68 percent / water; triethylamine / 0.17 h / 140 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thiophosphorylated amine resin In toluene at 90℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.78 g | With sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.24 g | With sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In tetrahydrofuran; diethyl ether at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: Et3N / CH2Cl2 / Heating 2.1: CH2Cl2 2.2: 84 percent / aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: Et3N / CH2Cl2 / Heating 2.1: CH2Cl2 2.2: 84 percent / aq. HCl 3.1: TFA / CH2Cl2 / 0.5 h 3.2: 78 percent / diethylamine / CH2Cl2 / 0.75 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / diethyl ether; tetrahydrofuran / 15 h / 20 °C 2: 52 percent / BOP; i-Pr2NEt / CH2Cl2 / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / diethyl ether; tetrahydrofuran / 15 h / 20 °C 2: 52 percent / BOP; i-Pr2NEt / CH2Cl2 / 16 h / 20 °C 3: 68 percent / LiBH4 / tetrahydrofuran / 2 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2.78 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C 2: 2.24 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2.78 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C 2: 2.24 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C 3: 1.11 g / EDC; HOBt / dimethylformamide / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 2.78 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C 2: 2.24 g / EDC; HOBt; aq. NaOH / dimethylformamide / 0 - 20 °C 3: 1.11 g / EDC; HOBt / dimethylformamide / 0 - 20 °C 4: 97 percent / BBr3 / CHCl3; CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 73 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: diethyl ether 3: H2 / Pd/C / methanol / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 73 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 70 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 93 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 93 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 94 percent / diethyl ether 3: 92 percent / H2 / Pd/C / methanol / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 94 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 73 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C 5: 89 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: diethyl ether 3: H2 / Pd/C / methanol / 760.05 Torr 4: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C 5: 90 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 70 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 93 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 72 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C 5: 92 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 60 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C 5: 92 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 61 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 94 percent / diethyl ether 3: 92 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 70 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C 5: 90 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: diethyl ether 3: H2 / Pd/C / methanol / 760.05 Torr 4: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 73 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 70 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 93 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 72 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 60 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 95 percent / diethyl ether 3: 90 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 73 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 61 percent / Me3Al / hexane; 1,2-dichloro-ethane / 24 h / Heating 2: 94 percent / diethyl ether 3: 92 percent / H2 / Pd/C / methanol / 760.05 Torr 4: 70 percent / EDCI; HOBt / dimethylformamide / 14 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / SO2Cl2 2: BOP, triethylamine / acetonitrile / 4 h / Ambient temperature 3: 80 percent / H2 / Pd/C / ethyl acetate / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84.4 percent / conc. H2SO4 / dioxane / 5.25 h / 25 °C 2: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 to -20 deg C, 1 h, 2.) THF, DMF, 25 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84.4 percent / conc. H2SO4 / dioxane / 5.25 h / 25 °C 2: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 to -20 deg C, 1 h, 2.) THF, DMF, 25 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 84.4 percent / conc. H2SO4 / dioxane / 5.25 h / 25 °C 2: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 to -20 deg C, 1 h, 2.) THF, DMF, 25 deg C, 1 h 3: 86.1 percent / anisole / CH2Cl2 / 3.25 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 84.4 percent / conc. H2SO4 / dioxane / 5.25 h / 25 °C 2: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 to -20 deg C, 1 h, 2.) THF, DMF, 25 deg C, 1 h 3: 88.3 percent / anisole / CH2Cl2 / 3.25 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dimethylsulfoxide; dimethylformamide / 24 h 2: TFA, anisole | ||
Multi-step reaction with 2 steps 1: 71 percent / K2CO3, N-Methylpiperazine / H2O; acetonitrile; dimethylformamide / 2 h / Ambient temperature 2: 56 percent / NH3, pyridine / methanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dimethylsulfoxide; dimethylformamide / 24 h 2: TFA, anisole 3: Et3N / dimethylformamide / 48 h / 4 °C 4: 38 percent / methanesulfonic acid, thioanisole, o-cresol / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide / 48 h / 4 °C 2: 38 percent / methanesulfoniy acid, TFA, thioanisole, o-cresol / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfoxide; dimethylformamide / 24 h 2: TFA, anisole 3: Et3N / dimethylformamide / 48 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, triethylamine 2: AcOH-H2O, 2-propanol, H2 / Pd/C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AcOH / methanol / 48 h 2: HCl / 4 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; benzyl alcohol In dichloromethane; ethyl acetate | 8.a (a) (a) N-[N-[Phenylmethoxy(phenyl)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester A mixture of phenylphosphonic dichloride (1.15 ml., 8 mmole) and dry dichloromethane (15 ml.) under argon at 25° is treated dropwise with benzyl alcohol (0.83 ml., 1 eq.) and triethylamine (1.1 ml., 1 eq.) in dichloromethane (5 ml.) over a 20 minute period. A slight exotherm is observed. The reaction mixture is then refluxed for 15 minutes, cooled to 0° (ice bath), and L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt (1 eq.) is added. The heterogeneous mixture is treated dropwise with triethylamine (2.4 ml., 2.1 eq.) in dichloromethane (8 ml.) over a 5 minute period. The ice bath is removed and the reaction mixture is stirred for an additional 1.5 hours. The solids are removed by filtration and the dichloromethane is stripped from the filtrate. The residue is taken up in ethyl acetate and washed with water, saturated sodium bicarbonate, 5% potassium bisulfate, saturated sodium bicarbonate, brine, dried (MgSO4), and evaporated to a residue. The residue is purified chromatographically to give N-[N-[phenylmethoxy(phenyl)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Hg; phosphorus pentachloride; triethylamine In dichloromethane; ethyl acetate; benzene | 7.b (b) (b) N-[N-[Ethoxy(phenylmethyl)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester A mixture of phenylmethylphosphonic acid, diethyl ester (0.92 g., 4.04 mmole) and phosphorus pentachloride (0.85 g., 4.08 mmole) in dry benzene (7 ml.) is refluxed under argon for one hour. The cooled solution is evaporated to dryness at room temperature (0.5 mm. of Hg), taken up in dry benzene (about 5 ml.) and again evaporated to dryness. The colorless residue is then taken up in dry dichloromethane (10 ml.) and treated with L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt. The resulting suspension is cooled to 0° (ice bath) under argon and treated dropwise with a solution of triethylamine in dry dichloromethane over a period of 15 minutes. After the addition is complete, the ice bath is removed and the mixture is allowed to stir at room temperature for 30 minutes. The mixture is diluted with ethyl acetate, filtered and evaporated to dryness. The residue is taken up in ethyl acetate and washed successively with 5% potassium bisulfate, saturated sodium bicarbonate, saturated sodium chloride, dried (Na2 SO4) and evaporated. The residue is purified by flash chromatography on silica gel to give N-[N-[ethoxy(phenylmethyl)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.e (e) (e) N-[N-[(2-Phenylethyl)(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester (2-Phenylethyl)phosphinic acid, phenylmethyl ester is reacted with L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt according to the procedure of Example 1(c) to yield N-[N-[(2-phenylethyl)(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.b (b) (b) N-[N-[Hexyl(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester Hexylphosphinic acid, phenylmethyl ester is reacted with L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt according to the procedure of Example 1(c) to yield N-[N-[hexyl(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.b (b) (b) N-[N-[Octyl(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester Octylphosphinic acid, phenylmethyl ester is reacted with L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt according to the procedure of Example 1(c) to yield N-[N-[octyl(phenylmethoxy)phosphinyl]-L-phenylalanyl]-L-leucine, phenylmethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.d (d) (d) N-[N-[Hydroxy(3-phenylpropyl)phosphinyl]-L-phenylalanyl]-L-leucine, di(phenylmethyl)ester (3-Phenylpropyl)phosphinic acid, phenylmethyl ester is reacted with L-phenylalanyl-L-leucine, phenylmethyl ester, hydrochloride salt according to the procedure of Example 1(c) to give N-[N-[hydroxy(3-phenylpropyl)phosphinyl]-L-phenylalanyl]-L-leucine, di(phenylmethyl)ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17 EXAMPLE 17 EXAMPLE 17 According to the same procedure as in Example 13 except that 1-(1(S) -t-butoxycarbonyl-3-methylbutyl)-3-azido-4-phenylazetidin-2-one (358 mg., 1.0 mmol) was used as a starting material, hydrochloride of t-butyl ester of D/L-phenylalanyl-L-leucine was obtained in a quantitative yield. IR (KBr): 3210, 1740, 1680, 1560, 1150 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol | 19 EXAMPLE 19 EXAMPLE 19 1-(1(S)-Benzyloxycarbonyl-3-methylbutyl)-3-azido-4-phenylazetidin-2-one (200 mg., 0.51 mmol) was hydrogenated in 10 ml. of ethanol at 50° C. for 19 hours under ambient pressure using a 10% Pd-C (270 mg.) as a catalyst to give D/L-phenylalanyl-L-leucine quantitatively. IR (KBr): 3210, 1670, 1580 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium iodide; sodium hydrogencarbonate In <i>N</i>-methyl-acetamide | 5.e (e) (e) (S)-N-[N-[3-(benzoylamino)-2-oxobutyl]-L-phenylalanyl]-L-leucine,1,1-dimethylethyl ester To a stirred solution of L-phenylalanyl-L-leucine, 1,1-dimethylethyl ester (3.48 g., 10 mmole) in 20 ml. of dimethylformamide (under argon) is added (S)-3-(benzoylamino)-1-chloro-2-butanone (2.26 g., 10 mmole), sodium iodide (375 mg., 2.5 mmole), and sodium bicarbonate (840 mg., 10 mmole). The reaction mixture is stirred for 10 minutes and then an additional 20 ml. of dimethylformamide is added. After 2.5 hours the reaction has completed. The dimethylformamide is evaporated in vacuo and the residue is taken up into ether (35 ml.), washed with half-saturated sodium bicarbonate (2*50 ml.) and brine (2*25 ml.), dried (mixture of MgS04 and Na2 SO4), and evaporated to give 6.02 g. of a yellow oil which darkens to orange over 2 hours. This material is applied to a column of 300 g. of silica gel (230-400 mesh) and eluted with ethyl acetate-hexane (3:2). Fractions 21-27 (approximately 50 ml. each) are pooled giving 2.26 g. of crude product. This material is applied to a second column of silica gel (LPS-1, 130 g.) and eluted with 3 l. of hexane-ethyl acetate (2:1) then 2 l. of hexane-ethyl acetate (1:1). Fractions 61-100 (approximately 30 ml. each) are pooled and evaporated yielding 1.39 g. of product. One recrystallization from ethyl acetate gives 900 mg. of (S)-N-[N-[3-(benzoylamino)-2-oxobutyl]-L-phenylalanyl]-L-leucine, 1,1-dimethylethyl ester as a white, powdery solid; m.p. 46°-50°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium iodide; sodium hydrogencarbonate In <i>N</i>-methyl-acetamide; ethyl acetate | 1.C (C) To a stirred solution of L-phenylalanyl-L-leucine, t-butyl ester (6 mmol) in 10 ml of dimethylformamide (under argon) was added a solution of [(S)-3-chloro-1-methyl-2-oxopropyl]- carbamic acid, 1,1-dimethylethyl ester (1.33 g, 6 mmol) in 20 ml of dimethylformamide, followed by sodium iodide (450 mg, 3 mmol) and sodium bicarbonate (504 mg,. 6 mmol). The reaction mixture was allowed to stir for 15 hours, and the solvent was then evaporated (<25° C., vacuum pump). The yellow residue was taken up into ethyl acetate (250 ml) and washed with water (4*25 ml) and brine (25 ml), then dried (sodium sulfate) and evaporated to a yellow residue (3.44 g). This was applied to a column of silica gel (Merck, 230-400 mesh, 250 g) and eluted with hexane-ethyl acetate (1.25:1). Fractions 25-40 (~30 ml each, homogeneous on TLC) were pooled and concentrated yielding 2.29 g of a colorless oil. Rapid recrystallization from ethyl acetate-hexane afforded 1.61 g of the title compound as a powdery white solid. |