Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 2578-57-6 | MDL No. : | MFCD00022391 |
Formula : | C7H12N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RNKSNIBMTUYWSH-YFKPBYRVSA-N |
M.W : | 172.18 | Pubchem ID : | 6426709 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.71 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 45.14 |
TPSA : | 78.43 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -10.06 cm/s |
Log Po/w (iLOGP) : | 0.81 |
Log Po/w (XLOGP3) : | -3.81 |
Log Po/w (WLOGP) : | -1.44 |
Log Po/w (MLOGP) : | -1.03 |
Log Po/w (SILICOS-IT) : | -0.4 |
Consensus Log Po/w : | -1.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.76 |
Solubility : | 9830.0 mg/ml ; 57.1 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 2.76 |
Solubility : | 98000.0 mg/ml ; 569.0 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.58 |
Solubility : | 44.8 mg/ml ; 0.26 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.91 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogen In methanol; water | |
With ethanol; palladium; acetic acid Hydrogenation; | ||
With ethanol; palladium; acetic acid Hydrogenation.Reagens 4: Platin; |
With methanol; palladium; acetic acid Hydrogenation; | ||
With palladium 10% on activated carbon; hydrogen In methanol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 31 Example 31: Synthesis of 2-formyl-pyrrolidinyl-glycine (SSJ-4): Dissolve SSJ-3 (1g, 3.67mmol) in 100mL of dichloromethane solution, add trifluoroacetic acid (10mL, 143mmol) dropwise at 0°C, react under nitrogen protection for 2h at room temperature, and concentrate under reduced pressure to obtain a light yellow slurry SSJ-4 (625 mg, 98% yield) |
345 mg | Stage #1: N-tert-butyloxycarbonyl-L-prolylglycine With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: | Synthesis ofHN-Pro-Gly-OH (4) Boc-Pro-Phe-OMe, (1.0 g, 3.5 mmol, 1 eq.) was dissolved in minimum volume of methanol and NaOH (0.16 g, 4.2 mmol, 1.2 eq.) as its 1N solution was added and was stirred for 6 h. Then, solvent was evaporated and 20 mL of water was added to it in ice cold condition. The solution was acidified to pH 2-3 and extracted in dichloromethane. Dichloromethane was dried over anhydrous sodium sulphate, filtered and evaporated to get product Boc-Pro-Gly-OH which was directaly used for Boc deprotection. The acid t-Boc-Pro-Gly-OH, (0.85 g, 3.1 mmol, 1 eq) was dissolved in 75% Trifluoroacetic acid - Dichloromethane (15 mL) and set aside for 1 h under N2 atmosphere. Solvent was evaporated in high vacuuo, washed with diethyl ether (3x50 mL). White-brownish viscous product was obtained which was washed with boiling ether (50 mL) then cold ether ether. The White-brownish viscous product, (0.87 g,), was obtained which passed through the strong anion exchange resin to get product 4 (345 mg). |
With trifluoroacetic acid In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With hydrogen; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibenzoyl peroxide In dimethyl sulfoxide Ambient temperature; Irradiation; other solvents; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With sodium carbonate In tetrahydrofuran; water for 24h; Ambient temperature; pH 9-9.2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In acetic anhydride; ethyl acetate for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorine at 24.85℃; for 2.77778E-05h; Irradiation; solvent isotope effect; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 4℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 4℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dimethyl ether-poly(hydrogen fluoride) at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; hydrogen cation In various solvent(s) at 19.85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C 3: 80 percent / HBr / acetic acid / 0.33 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C 3: 80 percent / HBr / acetic acid / 0.33 h 4: 40 percent / NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C 5: HBr / acetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C 3: 80 percent / HBr / acetic acid / 0.33 h 4: 40 percent / NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C 3: 80 percent / HBr / acetic acid / 0.33 h 4: 40 percent / NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C 5: HBr / acetic acid / 20 °C 6: NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C 7: HBr / acetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 90 percent / K2CO3 / H2O 2: 75 percent / N-methylmorpholine; isobutylchloroformiate / tetrahydrofuran / 0.17 h / -10 °C 3: 80 percent / HBr / acetic acid / 0.33 h 4: 40 percent / NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C 5: HBr / acetic acid / 20 °C 6: NaHCO3 / 1,2-dimethoxy-ethane; H2O / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 2 h / 4 °C 2: N,N'-diisopropylcarbodiimide; 1-hydroxybenzotriazole / acetonitrile / 4 °C 3: aq. HCl / dioxane / 8 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 2 h / 4 °C 2: N,N'-diisopropylcarbodiimide; 1-hydroxybenzotriazole / acetonitrile / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 4 h / 4 °C 2: EDCI*HCl; Et3N / acetonitrile / 16 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 4 h / 4 °C 2: EDCI*HCl; Et3N / acetonitrile / 16 h / 4 °C 3: HCl(g) / dioxane / 96 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetone / 4 h / 4 °C 2: EDCI*HCl; Et3N / acetonitrile / 16 h / 4 °C 3: HCl(g) / dioxane / 96 h / 4 °C 4: NH3 / methanol; ethanol / 4 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / ethyl acetate; dimethylformamide / 2 h / -10 - 20 °C 2: 76 percent / NaOH; HCl / acetone / 2 h 3: 95 percent / H2 / 10 percent Pd/C / H2O; methanol | ||
Multi-step reaction with 2 steps 1: 1) NMM, ECF / 1) THF, -5 deg C, 10 min, 2) CHCl3, 0 deg C, 1 h; r.t., overnight 2: 87 percent / acetic acid, H2 / Pd black | ||
Multi-step reaction with 3 steps 1: pyridine; PCl3 2: aqueous NaOH; dioxane 3: palladium; acetic acid; aqueous methanol / Hydrogenation |
Multi-step reaction with 3 steps 1: diethyl ether; PCl3 2: diethyl ether; aqueous NaOH 3: palladium; acetic acid; aqueous ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 76 percent / NaOH; HCl / acetone / 2 h 2: 95 percent / H2 / 10 percent Pd/C / H2O; methanol | ||
Multi-step reaction with 2 steps 1: aqueous NaOH; dioxane 2: palladium; acetic acid; aqueous methanol / Hydrogenation | ||
Multi-step reaction with 2 steps 1: aqueous NaOH; acetone 2: palladium; acetic acid; aqueous methanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 6 h / 20 °C 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.2: strong anion exchange resin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2O / Irradiation 2: H2O / 210 °C / gas phase spectrum | ||
Multi-step reaction with 3 steps 1: H2O / Irradiation 3: 1.) H2 / multistep reaction; gas phase spectrum |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2O / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethyl ether; aqueous NaOH 2: palladium; acetic acid; ethanol / Hydrogenation.Reagens 4: Platin | ||
Multi-step reaction with 2 steps 1: diethyl ether; aqueous NaOH 2: palladium; acetic acid; aqueous ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: aqueous NaOH 2: pyridine; PCl3 3: aqueous NaOH; dioxane 4: palladium; acetic acid; aqueous methanol / Hydrogenation | ||
Multi-step reaction with 3 steps 3: ethanol; aqueous NaOH | ||
Multi-step reaction with 4 steps 1.1: triethylamine / methanol / 20 - 65 °C 2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 1 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / methanol / 6 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 4.2: strong anion exchange resin |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 3 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 25 °C 3: sodium hydrogencarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; 1,4-dioxane / 12 h / 25 °C 4: trifluoroacetic acid / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In N,N-dimethyl-formamide at 200℃; for 0.333333h; Microwave irradiation; | |
88% | With Zr6-based UiO-66 metal-organic frameworks at 80℃; for 24h; | |
76% | With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h; |
Multi-step reaction with 2 steps 1: HCl 2: 105 °C / 0 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: palladium; acetic acid; methanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: concentrated aqueous NH3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: ethanol; aqueous NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.b (b) (b) N-(L-Prolyl)glycine, phenylmethyl ester, hydrochloride salt The product from part (a) (2.3 g., 6.3 mmole) is treated with trifluoroacetic acid (5 ml.) at 25° in an argon atmosphere for 1 hour. The trifluoroacetic acid is removed in vacuo and the residue taken up in ether (15 ml.). The ethereal solution is treated with a saturated hydrochloric acid/ether solution in small portions precipitating the hydrochloride salt. The ether is decanted and the residue is triturated with ether (5 times) then dried in vacuo for 24 hours to give 1.9 g. of N-(L-prolyl)glycine, phenylmethyl ester, hydrochloride salt as a hydroscopic foam. Tlc (dichloromethane/methanol/acetic acid; 8:1:1) shows a single spot at Rf 0.6. Anal. calc'd for C14 H19 N2 O3 Cl.1.3 H2 O: C, 52.07; H, 6.77; N, 8.67; Cl, 10.98 Found: C, 52.06; H, 6.38; N, 8.44; Cl, 10.63. | ||
L-proline N-octylamide and also the stereoisomers thereof and the organic or mineral salts and solvates thereof, and also the following amino acids and derivatives: ... H-PRO-ALA-OH H-PRO-β-ALA-OH H-PRO-GLY-NH2 H-PRO-GLY-OH H-PRO-GLY-OH H-PRO-ILE-OH H-PRO-LEU-OH H-PRO-NHCH3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride; triethylamine In dichloromethane; benzene | 13.c (c) (c) N-[1-[Ethoxy(4-phenylbutyl)phosphinyl]-L-prolyl]glycine, phenylmethyl ester A mixture of (4-phenylbutyl)phosphonic acid, diethyl ester (1.7 g., 6.4 mmole), benzene (10 ml.), and phosphorus pentachloride (1.3 g., 1 eq.) are reflexed under argon for 45 minutes. The benzene and phosphorus oxychloride are removed in vacuo. The residue is taken up in dry dichloromethane (10 ml.), cooled to 0° (ice-bath) and treated with N-(L-prolyl)glycine, phenylmethyl ester, hydrochloride salt (1.9 g., 6.36 mmole). The resulting suspension is treated dropwise with a solution of triethylamine (2.7 ml., 3 eq.) in dichloromethane (5 ml.) under argon. The ice-bath is removed and the heterogeneous mixture is stirred for 1.5 hours. The reaction mixture is diluted with ethyl acetate and washed successively with water (twice), 5% potassium bisulfate, saturated sodium bicarbonate, brine, dried (MgSO4), and evaporated. The residue (3 g.) is chromatographed on silica (80 g.) eluding with hexane/acetone (5/2) followed by elution with hexane/acetone (2/1) to give 1.65 g. of N-[1-[ethoxy(4-phenylbutyl)phosphinyl]-L-prolyl]glycine, phenylmethyl ester as a yellow oil. Tlc (hexane/acetone; 2:1) shows two spots (isomers at phosphorus) Rf 0.3, 0.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaOH In methanol Cr-complex was refluxed with 3 equiv of peptide for 2 h, 4 equiv of NaOH was added, refluxed for 26 h; sepd. by chromy. on silica gel column, eluted with MeOH, crystd. from concd. MeOH soln. diluted with acetone, cooled; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; potassium chloride; lead dioxide In water dissolving of peptides mixture in water, aq. NaOH addn. to pH 9-9.5, aq. CoCl2 dropwise addn. (keeping pH at 9 with aq. NaOH), stirring with PbO2 at 40°C for 1 h, filtration, chromy. (QAE-Sephadex/Cl(1-) form, H2O then 0.05M KCl); concn. at 35-40°C, CH3OH addn., filtration, concn., chromy. (Sephadex G-10), concn., C2H5OH addn. to aq. soln. (or acetone addn. to CH3OH soln.), cooling, filtration, washing with C2H5OH then acetone (or withacetone), vac. drying, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; potassium chloride; lead dioxide In water dissolving of peptide in water, aq. NaOH addn. to pH 9-9.5, aq. CoCl2 dropwise addn. (keeping pH at 9 with aq. NaOH), stirring with PbO2 at 40°C for 1 h, filtration, chromy. (QAE-Sephadex A-25/Cl(1-), H2O then 0.05M KCl); concn. at 35-40°C, CH3OH addn., filtration, concn., chromy. (Sephadex G-10), concn., C2H5OH addn. to aq. soln. (or acetone addn. to CH3OH soln.), cooling, filtration, washing with C2H5OH then acetone (or withacetone), vac. drying, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol byproducts: KCl; ligand (1 equiv.) added to suspn. of Cr complex in MeOH; heated at 65°C for 1.5 h with stirring; KOH added; heated for 1.5 h; cooled; filtered; soln. evapd. to dryness; dissolved in min. H2O; passed through Sephadex G-10 column; first violet (Cr(L-progly)2(1+)) and second brownish bands collected; brownish band concd.; treated with satd. LiClO4-Et2O; held at room temp. for several d; crystals washed with EtOH; air dried; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 0.0833333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With d-(5′-CCGCCATGGAGTTGAAACAAGGAAC-3*5′-TTAAAAGCTTTTTTTGATTAAAGCTGCCA-3′); water In aq. phosphate buffer at 25℃; | 2.7. Substrate specificities and enzyme kinetics General procedure: A variety of peptides were examined as the substrates, includingPro-Pro, Pro-Glu, Pro-Met, Pro-Ser, Pro-Arg, Pro-Phe, Pro-Leu, Pro-Gly,Met-Ala, Leu-Leu, Leu-Gly-Gly, and Pro-Gly-Gly. Substrate specificitieswere examined for all these peptides at 2mMsubstrate. Enzyme kineticparametersweremeasured for Pro-Xaa substrates under optimum conditions:in 50mMHEPES buffer (pH 7.5) and at 25 °C for r-PepR1; and in50mMHEPES buffer (pH 8.0) and at 30 °C for r-PepR2. Enzyme kineticvalues Km and kcat were obtained using a method described by Sakodaand Hiromi [15] for each substrate. All experiments were conducted intriplicate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 %Chromat. | Stage #1: tetrabutylphosphonium glycinate; L-proline methyl ester monohydrochloride at 60℃; for 30h; Inert atmosphere; Stage #2: With acetic acid In chloroform at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 1 h / 0 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / methanol / 6 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.2: strong anion exchange resin | ||
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 25 °C 2: sodium hydrogencarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; 1,4-dioxane / 12 h / 25 °C 3: trifluoroacetic acid / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.7% | With palladium 10% on activated carbon; hydrogen; triethylamine In methanol; water at 25℃; for 12h; | Methyl-L-prolylglycine (B4) Formaldehyde (40%, 2.4 mL, 31.8 mmol) and 10% palladium on carbon (0.35 g) were added to Compound 9h (3.5 g, 12.2 mmol) in methanol (30 mL), under a hydrogen atmosphere. After stirring at 25 °C for 12 h, the reaction mixture was filtered, and the filtrate was concentrated. Water (25 mL) was added to the residual oil, followed by sodium hydroxide (1 M), and pH was adjusted to 13-14. After the mixture was washed with dichloromethane, the aqueous layer was adjusted to pH 2 by saturated aq. potassium bisulfate, and then concentrated under reduced pressure to generate Compound B4 (2.1 g, 93.7%) as oil. 1H NMR (500 MHz, CD3OD), δ 4.14 (t, J = 8.3, 1H), 4.00 (s, 2H), 3.71 (ddd, J = 11.4, 7.7, 4.1, 1H), 3.22 (d, J = 11.1, 1H), 2.95 (d, J = 10.5, 3H), 2.58 (dd, J = 12.2, 7.5, 1H), 2.24-2.02 (m, 3H). 13C NMR (125 MHz, D2O), δ 22.45, 29.04, 40.36, 41.18, 56.45, 68.62, 168.96, and 172.68 ppm. HRMS (ESI), m/z 187.1079 [M + H]+ (Calcd for C8H14N2O3,187.1077). |
93% | With palladium 10% on activated carbon; hydrogen In methanol at 20℃; | 32 Example 32: Synthesis of (N-methyl-pyrrolidin-2-formyl)-glycine (SSJ-G): Dissolve SSJ-4 (2g, 11.71mmol, 1eq) in 50mL methanol solution, add 40% formaldehyde solution (1mL, 12.88mmol, 1.1eq), palladium on carbon (10%, 350mg), plus hydrogen protection device After ventilating for 2-3 times, stirring overnight at room temperature, after treatment, filter off the palladium carbon with diatomaceous earth on a triangular funnel, concentrate the filtrate to obtain a crude product, add 20 mL of water to dissolve, adjust the pH to about 13 with saturated sodium hydroxide solution, and wash with DCM. Saturated KHSO4 solution adjusted pH=2, concentrated under reduced pressure to obtain SSJ-G (2.0g, yield 93%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; 1,4-dioxane / 12 h / 25 °C 2: trifluoroacetic acid / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With sodium hydroxide In water at 25℃; for 120h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C 2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C 2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere 3.2: 0.17 h / 20 °C |