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CAS No. : | 54594-06-8 | MDL No. : | MFCD00063104 |
Formula : | C5H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WNNNWFKQCKFSDK-SCSAIBSYSA-N |
M.W : | 115.13 | Pubchem ID : | 6992334 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 30.15 |
TPSA : | 63.32 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) : | -8.61 cm/s |
Log Po/w (iLOGP) : | 0.91 |
Log Po/w (XLOGP3) : | -2.26 |
Log Po/w (WLOGP) : | -0.03 |
Log Po/w (MLOGP) : | -2.31 |
Log Po/w (SILICOS-IT) : | -0.38 |
Consensus Log Po/w : | -0.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.07 |
Solubility : | 1350.0 mg/ml ; 11.7 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.46 |
Solubility : | 3350.0 mg/ml ; 29.1 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.26 |
Solubility : | 210.0 mg/ml ; 1.82 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 | ||
With hydrogenchloride In water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide at 37℃; for 16h; amino peptidase from Pseudomonas putida, pH 8.2; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methyloxirane In ethanol for 0.25h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrogenchloride; methyloxirane 1.) 1 h, reflux, 2.) EtOH, 15 min, reflux; | |
Multi-step reaction with 2 steps 1: 6N aq. HCl / 1 h / Heating 2: methyloxirane / ethanol / 0.25 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With toluene-4-sulfonic acid In benzene for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonia; lithium In tetrahydrofuran; ethanol for 1h; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrazine hydrate In ethanol; acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With water for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In methanol at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With boron trifluoride diethyl etherate In acetonitrile at 0℃; for 1h; | |
With boron trifluoride diethyl etherate In acetonitrile for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride at 70℃; | 18.3 A solution of (/7)-2-aminopent-4-enoic acid (18d) (5 g, 43.5 mmol) in MeOH HCi (2.4M, 50 mL) was stirred at 70°C overnight. The mixture was concentrated under reduced pressure to give compound 18e (5.5 g, 98% yield), which was used without purification. |
With thionyl chloride at 60℃; for 3h; | ||
With acetyl chloride for 4h; Reflux; Inert atmosphere; |
With thionyl chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; water Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.2% | With sodium hydroxide In 1,4-dioxane at 20℃; for 18h; Cooling with ice; | |
61% | With sodium hydrogencarbonate In 1,4-dioxane; water for 5h; | |
59% | With sodium hydroxide In 1,4-dioxane; water for 0.5h; Cooling with ice; |
In 1,4-dioxane; water Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In water for 10h; Heating; other reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 62% 2: 80% | With hydrogenchloride at 90℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 63% 2: 71% | With hydrogenchloride at 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride for 16h; | 2 Methyl (2/)-2-amino-4-pentenoate hydrochloride (38); To a suspension of (27?)-2-amino-4-pentenoic acid (200 mg, 1.74 mmol) in methanol (6 mL) at O0C was added dropwise thionyl chloride (1 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product crystallized with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (287 mg, 1.74 mmol, 100%) as a white solid which had spectral data in agreement with that reported.123 Mp 135-14O0C. 1H NMR (CDCl3, 300 MHz): δ 8.70 (bs, 3H, NH3+); 5.89 (m, IH, H4); 5.32 (d, J = 17.3 Hz, IH, H5a); 5.24 (d, / = 10.1 Hz, IH, H5b); 4.31 (m, IH, H2); 3.81 (s, 3H, OCH3); 2.87 (t, J = 6.3 Hz, 2H, H3). Mass Spectrum (ES, +ve) m/z 130 (100%) [M+]. HRMS calcd for C6Hi2NO2 130.0868, found 130.0870. |
100% | With thionyl chloride at 0 - 20℃; for 16h; | |
100% | With thionyl chloride at 0 - 20℃; | a D-allylglycine (5.03g, 43.73 mmol, 1.0 equiv) is slurried in a suspension of methanol (70 mL) in an ice-water bath. Thionyl chloride (9.6 mL, 131.19 mmol, 3.0 equiv.) is added dropwise over 10 minutes. The reaction is warmed to room temperature until complete as shown by LC/MS. The solvent is evaporated and the resulting white solid of 5- A is directly used in the next step. |
100% | With thionyl chloride at 0 - 20℃; for 22h; | |
99% | With thionyl chloride for 6.5h; | |
With thionyl chloride for 4h; Heating; | ||
With thionyl chloride at 0 - 20℃; for 0.166667h; | 9.a 9-A: D-allylglycine (5.03 g, 43.73 mmol, 1.0 equiv) is slurried in a suspension of methanol (70 mL) in an ice-water bath. Thionyl chloride (9.6 mL, 131.19 mmol, 3.0 equiv.) is added dropwise over 10 minutes. The reaction is warmed to room temperature and judged to completeness by LC/MS. The solvent is evaporated and the resulting white solid of 9-A is directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine In water; acetonitrile for 2h; | |
With sodium hydrogencarbonate In water; acetone at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hydroxide In tetrahydrofuran; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: allyl iodid; C15H22N2O2S2 With tetrabutylammomium bromide; sodium ethanolate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; Stage #3: In water at 100℃; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With Rhodococcus erythropolis NCIMB 11540 (whole cells, amidase) In phosphate buffer at 37℃; for 3h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: glycine With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate In methanol for 0.333333h; Heating; Stage #2: allyl bromide With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl In dichloromethane at 20℃; for 0.5h; Stage #3: With hydrogenchloride In methanol; water Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: glycine With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate In methanol for 0.333333h; Heating; Stage #2: allyl iodid With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl In dichloromethane at 20℃; for 0.0666667h; Stage #3: With hydrogenchloride In methanol; water Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: (1R,2S,5R,8S)-5-allyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one With hydrogenchloride at 87℃; for 2h; Stage #2: With methyloxirane In ethanol at 20℃; for 0.5h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79 % Chromat. | With borane-ammonia complex; oxygen; ammonium formate In water for 5h; | |
Multi-step reaction with 3 steps 1: aq. NaOH solution 2: mit Hilfe eines Enzyms aus Schweine-Nieren 3: aqueous HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 1.5h; Stage #2: allyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78℃; for 14h; Stage #3: With hydrogenchloride at 87℃; for 2h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (3R,6S)-3-allyl-6-tert-butyl-5-methoxy-6-methyl-3,6-dihydro-2H-1,4-oxazin-2-one With trifluoroacetic acid In water; acetonitrile at 60℃; for 20h; Stage #2: With sodium hydroxide In water at 20℃; for 20h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride In methanol; dichloromethane; water at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With lithium hydroxide In tetrahydrofuran at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With water; triethylamine; In 1,4-dioxane; at 20℃; | To a suspension of D-2-amino-4-pentenoic acid (500 mg) in Dioxane (20 mL) at RT was added triethylamine (1.09 g), water (0. 5 mL), and N- (BENZYLOXYCARBONYLOXY) SUCCINIMIDE (2.27 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NAHCO3 and extracted with ether (3x). The basic aqueous layer was acidified to pH 2 with 2N HCI and extracted with EtOAc (3x). The combined EtOAc layer was washed with brine, dried (NA2S04), filtered and concentrated to give a clear viscous oil (1.17 g, quantitative). H NMR (300 MHz, DMSO-d6) 8 2.29-2. 50 (M, 2H), 3.98-4. 06 (M, 1H), 5.03 (s, 2H), 5.05-5. 12 (M, 2H), 5. 71-5. 84 (m, 1H), 7.35 (M, 5H), 7.54 (d, 1H), 12.57 (bs, 1H). MS APCI, m/z = 250 (M+1). LC/MS 1.90 min. , Method A. |
76% | With triethylamine; In tetrahydrofuran; water; at 20℃; | D-allylglycine (2.07 g, 18.0 mmol) and N-(benzyloxycarbonyloxy)succinimide (Cbz-OSu) (4.49 g, 18.0 mmol) are added to a round bottomed flask containing THF (60 mL) and water (20 mL). The mixture is stirred at room temperature and Et3N (10.1 mL, 72.0 mmol) is added, and the reaction is stirred overnight at room temperature. The clear solution is diluted with EtOAc (200 mL), washed with IN HCl (3 x 100 mL) and brine (1 x 100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford 10-B as a white solid, which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaHCO3 / acetone; H2O / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaHCO3 / acetone; H2O / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; NaHCO3 / H2O; dioxane / 0 °C 2: 561 mg / BOP; DIPEA / CH2Cl2 / 0 °C 3: 70 percent / TsOH / toluene / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; NaHCO3 / H2O; dioxane / 0 °C 2: 561 mg / BOP; DIPEA / CH2Cl2 / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide; NaHCO3 / H2O; dioxane / 0 °C 2: 561 mg / BOP; DIPEA / CH2Cl2 / 0 °C 3: 70 percent / TsOH / toluene / 1 h / Heating 4: 83 percent / HBr; glacial acetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating 5: H2 6: LiOH; water / tetrahydrofuran; methanol / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating 5: H2 6: LiOH; water / tetrahydrofuran; methanol / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating 5: H2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 99 percent / SOCl2 / 6.5 h 2: HATU; DIPEA / CH2Cl2 / 20 °C 3: HATU; DIPEA / CH2Cl2 / 20 °C 4: bis(tricyclohexylphosphine)benzylidenerutheniumIV dichloride / CH2Cl2 / 2 h / Heating 5: H2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 2 h / Heating 2: dioxane / 18 h / 20 °C | ||
Multi-step reaction with 2 steps 1: hydrogenchloride / 70 °C 2: triethylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: methanol / 2 h / Heating 2: Et3N / 18 h / 20 °C 3: NaBH4 / methanol / 0.5 h / 0 °C | ||
Multi-step reaction with 2 steps 1: SOCl2 / 3 h / 60 °C 2: LiI, NaHCO3 / acetonitrile / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 2 h / Heating 2: Et3N / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol / 2 h / Heating 2.1: dioxane / 18 h / 20 °C 3.1: DIBAL-H / toluene / 2 h / -78 °C 4.1: CH2Cl2 / 48 h / -20 °C 4.2: Bu4NF*3H2O / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / 2 N aq. NaOH / acetone / pH 9.0, 0 deg C to r.t., overnight 2: TsOH / 6 h / Heating | ||
Multi-step reaction with 2 steps 1: 100 percent / NaHCO3 / H2O / 7 h / Ambient temperature 2: 89 percent / diethyl ether / 0.25 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: thionyl chloride 2: sodium hydrogencarbonate / 1,4-dioxane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / 4 h / Heating 2: pyridine / 24 h / 40 °C 3: 73 percent / SnCl4 / CH2Cl2 / 20 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: SOCl2 / 4 h / Heating 2: pyridine / 24 h / 40 °C 3: 11 percent / SnCl4 / CH2Cl2; acetonitrile / 18 h / 50 °C | ||
Multi-step reaction with 3 steps 1: SOCl2 / 4 h / Heating 2: pyridine / 24 h / 40 °C 3: 1.) HCOOH; 2.) NH3 / 1.) 50 deg C, 18 h; 2.) MeOH, 0 deg C, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 82 percent / Et3N, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 82 percent / Et3N, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride 3: 83 percent / DCC, DMAP, DMAP*HCl 4: 35 percent / bis(tricyclohexylphosphine)benzylideneruthenium dichloride / CH2Cl2 / 1) 1.5 h under Ar, 2) 2 h under air |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 88 percent / DCC, DMAP, DMAP*HCl / CH2Cl2 / 16 h / Heating 3: 100 percent / TBAF / tetrahydrofuran / 0.75 h 4: 1) Cu(OAc)2*H2O, 2) Pb(OAc)4 / 1) C6H6, 1 h, 2) C6H6, room temperature, 1 h; reflux, 15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 82 percent / Et3N, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride 3: 83 percent / DCC, DMAP, DMAP*HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 84 percent / DCC, DMAP, DMAP*HCl / CH2Cl2 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 84 percent / DCC, DMAP, DMAP*HCl / CH2Cl2 / Heating 3: 82 percent / NaIO4 / methanol; H2O / 14 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 88 percent / DCC, DMAP, DMAP*HCl / CH2Cl2 / 16 h / Heating 3: 100 percent / TBAF / tetrahydrofuran / 0.75 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61 percent / NaHCO3 / dioxane; H2O / 5 h 2: 88 percent / DCC, DMAP, DMAP*HCl / CH2Cl2 / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88 percent / H2 / Pd-C / methanol / 12 h / 760 Torr / Ambient temperature 2: 80 percent / BF3*Et2O / acetonitrile / 1 h / 0 °C | ||
Multi-step reaction with 2 steps 1: H2 / Pd/C / methanol / Ambient temperature 2: BF3*Et2O / acetonitrile / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) NaHCO3, 2) Amberlite IRC-50S / 1) H2O, 24 h, 2) H2O 2: 88 percent / H2 / Pd-C / methanol / 12 h / 760 Torr / Ambient temperature 3: 80 percent / BF3*Et2O / acetonitrile / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) NaOH, 2) Amberlite IRC-50S / 1) H2O, 24 h, 2) H2O 2: 88 percent / H2 / Pd-C / methanol / 12 h / 760 Torr / Ambient temperature 3: 80 percent / BF3*Et2O / acetonitrile / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 0.15 M aq. NaOH / Ambient temperature 2: H2 / Pd/C / methanol / Ambient temperature 3: BF3*Et2O / acetonitrile / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 85 percent / 2 N aq. NaOH / acetone / pH 9.0, 0 deg C to r.t., overnight 2: TsOH / 6 h / Heating 3: AIBN / toluene / 6 h / 65 °C 4: H2 / 10percent Pd/BaSO4 / acetic acid; H2O / 3 h / 50 - 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / 2 N aq. NaOH / acetone / pH 9.0, 0 deg C to r.t., overnight 2: TsOH / 6 h / Heating 3: AIBN / toluene / 6 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: conc. HCl / acetone / 2 h 2: 6 N aq. HCl / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 43 percent / PPh3, diethyl azodicarboxylate, phthalimide / tetrahydrofuran / 1.) -10 deg C, 3 h, 2.) 22 deg C, 15 h 2: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h 3: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C 4: 82 percent / Jones' reagent / acetone / 0 °C 5: 82 percent / hydrazine hydrate / ethanol; acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / Jones' reagent / acetone / 0 °C 2: 82 percent / hydrazine hydrate / ethanol; acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C 2: 82 percent / Jones' reagent / acetone / 0 °C 3: 82 percent / hydrazine hydrate / ethanol; acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h 2: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C 3: 82 percent / Jones' reagent / acetone / 0 °C 4: 82 percent / hydrazine hydrate / ethanol; acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 100 percent / NaHCO3 / H2O / 7 h / Ambient temperature 2: 89 percent / diethyl ether / 0.25 h / Ambient temperature 3: 33 percent / rhodium(II) acetate dimer / CH2Cl2 / Ambient temperature 4: 54 percent / 6N hydrochloric acid / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 100 percent / NaHCO3 / H2O / 7 h / Ambient temperature 2: 89 percent / diethyl ether / 0.25 h / Ambient temperature 3: 59 percent / rhodium(II) acetate dimer / CH2Cl2 / Ambient temperature 4: 90 percent / 6N hydrochloric acid / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / NaHCO3 / H2O / 7 h / Ambient temperature 2: 89 percent / diethyl ether / 0.25 h / Ambient temperature 3: 33 percent / rhodium(II) acetate dimer / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / NaHCO3 / H2O / 7 h / Ambient temperature 2: 89 percent / diethyl ether / 0.25 h / Ambient temperature 3: 59 percent / rhodium(II) acetate dimer / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With D-acylase; N-acetyl amino acid racemase G291D/F323Y for 18h; Enzymatic reaction; | |
Multi-step reaction with 2 steps 1: mit Hilfe eines Enzyms aus Schweine-Nieren 2: aqueous HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In methanol Heating / reflux; | 4 To a solution of 2-fluroronitrobenzene (3.70g, 26.06 mmol) and (2R)-2-amino- pent-4-enoic acid (3.00 g, 26.06 mmol) in MEOH (30 mL), was added NAHC03 (4.82 g, 57.33 mmol), and the reaction mixture was refluxed overnight. After cooling, concentrating, and chasing with benzene (3 x 30 ML), the crude product was dried on high vacuum pump overnight to give (2R)-2-[(2-nitrophenyl) amino] pent-4-enoic acid, which was then dissolved in MEOH, cooled to 0°C and saturated with HCl (g). The reaction was capped and the reaction mixture was stirred at room temperature overnight, concentrated, and then subjected to silica gel chromato- graphy eluting with 40%-60% CH2CL2 in hexanes to give methyl (2R)-2- [ (2-nitrophenyl)- AMINO] PENT-4-ENOATE (3.75g, 57% overall yield for 2 steps). Methyl (2R)-2- [ (2-NITROPHENYL)- amino] pent-4-enoate was dissolved in MEOH (70 mL) and SNCL2. H2O (16.84g, 74.63 mmol) was added. After refluxing overnight, the reaction mixture was cooled and concentrated under reduced pressure. The crude material was poured into EtOAc and saturated NAHC03 and extracted with EtOAc (3 x 100 mL). The combined organics were then washed with NAHC03 (1 x 50 mL) and brine (1 x 50 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 25%-40% EtoAc in Hexanes to give 1. 31G (47%) of (3R) -3-allyl-3, 4-dihydroquinoxalin-2 (1H)-ONE. LCMS (ES) NVZ 189.3 (M+H) +. | |
With sodium hydrogencarbonate In methanol Heating / reflux; | 4 EXAMPLE 4, (3R)-4-[(3,4-dichlorophenyl)sulfonyl]-3-{5-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenyl]pentyl}-3,4-dihydroquinoxalin-2(1H)-one To a solution of 2-fluroronitrobenzene (3.70 g, 26.06 mmol) and (2R)-2-aminopent-4-enoic acid (3.00 g, 26.06 mmol) in MeOH (30 mL), was added NaHCO3 (4.82 g, 57.33 mmol), and the reaction mixture was refluxed overnight. After cooling, concentrating, and chasing with benzene (3×30 mL), the crude product was dried on high vacuum pump overnight to give (2R)-2-[(2-nitrophenyl)amino]-pent-4-enoic acid, which was then dissolved in MeOH, cooled to 0° C. and saturated with HCl(g). The reaction vessel was capped and the reaction mixture was stirred at room temperature overnight, concentrated, and then subjected to silica gel chromatography eluting with 40% -60% CH2Cl2 in hexanes to give methyl (2R)-2-[(2-nitrophenyl)amino]pent-4-enoate (3.75 g, 57% overall yield for 2 steps). Methyl (2R)-2-[(2-nitrophenyl)amino]pent-4-enoate was dissolved in MeOH (70 mL) and SnCl2.H2O (16.84 g, 74.63 mmol) was added. After refluxing overnight, the reaction mixture was cooled and concentrated under reduced pressure. The crude material was poured into EtOAc and saturated NaHCO3 and extracted with EtOAc (3×100 mL). The combined organics were then washed with NaHCO3 (1×50 mL) and brine (1×50 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 25% -40% EtoAc in Hexanes to give 1.31 g (47%) of (3R)-3-allyl-3,4-dihydroquinoxalin-2(1H)-one. LCMS (ES) m/z 189.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(2R)-2-[(benzyloxy)carbonyl] amino }pent-4-enoic acid 42, prepared in one step from commercially available D-allyl glycine according to known procedures (J. Chem. Soc, 1962, 3963-3968), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: (R)-ethyl 2-((R)-1,1-dimethylethylsulfinamido)pent-4-enoate With hydrogenchloride In water at 90℃; for 4h; Stage #2: With methyloxirane In ethanol at 20℃; for 1h; optical yield given as %ee; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: methanol; D-allylglycine With thionyl chloride at 0 - 20℃; Inert atmosphere; Stage #2: di-<i>tert</i>-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 20h; basic pH; | Intermediate 52 methyl (2/?)-2-(IT(1.1-dimethylethyl)oxy1carbonyl)amino)-4-pentenoate To a suspension of (2R)-2-amino-4-pentenoic acid (6 g, 52.1 mmol, Aldrich) in dry methanol (60 ml) chilled at 00C by an ice bath under an argon atmosphere, thionyl chloride (7.61 ml, 104 mmol) was carefully added over 10 minutes keeping internal temperature below 100C. Solid dissolved and the homogeneous colourless solution was allowed to reach room temperature and left to stirr overnight. The mixture was evaporated to dryness and the residue was diluted in 1 ,4-Dioxane (60.0 ml) and sat. NaHCO3 solution was cautiously added in order to reach a basic pH and get the free base (a clear homogeneous solution was obtained). Di-te/f-butyl dicarbonate (14.52 ml, 62.5 mmol) was added portionwise and the mixture stirred for 20hours at room temperature, during which time some white solid precipitated. EtOAc (200ml) and water (50ml) were added and the phases were separated. The aqueous phase was further back-extracted with EtOAc (200ml) and finally the collected organics were washed with brine (50ml).After drying over Na2SO4 and evaporation of the solvent, 16g of crude material were recovered as colourless oil that was purified with SiO2 flash chromatography (biotage 65m) eluting with cyclohexane/AcOEt 9/1 (Rf=O.3). Evaporation of volatiles afforded title compound (12 g, 52.3 mmol, 100 % yield) as colourless oil. UPLC: Rt= 0.68mins, m/z= 230 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: D-allylglycine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Reflux; Stage #2: benzenesulfonyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.75h; | 2.3.a 1.0 g (8.68 mmol) of D-allylglycine (Peptech, Burlingtom, Mass.) was suspended in 50 ml of dry DCM, and 2.4 ml (19 mmol) of TMS-Cl and 3.3 ml (19 mmol) of DIEA were added. The mixture was refluxed for 1 h, the clear solution was cooled to 0° C., and 2.35 g (9.55 mmol) of Bzls-Cl and 1.8 ml of DIEA were added. The mixture was stirred at 0° C. for 15 min and at RT for 1.5 h. The solvent was removed in vacuo and the residue was dissolved in 700 ml of half-saturated NaHCO3 solution. The mixture was extracted 2× with ethyl acetate and then the aqueous phase was acidified with HCl (pH about 2-3). The mixture was extracted 3× with 150 ml of ethyl acetate, and the combined ethyl acetate phase was washed 2× with 5% KHSO4 solution and 1× with saturated NaCl solution. The organic phase was dried with Na2SO4, and the solvent was removed in vacuo.Yield: 2.2 g of oil (HPLC: 21.1 min, Start with 20% B)MS (ESI, m/e): 267 [M-1]- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: glycine With (R)-N-(2-benzoylphenyl)-1-(2-fluorobenzyl)pyrrolidine-2-carboxamide; sodium methylate; nickel(II) nitrate In methanol at 50℃; Inert atmosphere; Stage #2: allyl bromide With sodium hydroxide In N,N-dimethyl-formamide at 20 - 50℃; for 0.15h; optical yield given as %ee; enantioselective reaction; Further stages; |
[ 108412-04-0 ]
(R)-2-Aminopent-4-enoic acid hydrochloride
Similarity: 0.97
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