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[ CAS No. 1323290-64-7 ]

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Chemical Structure| 1323290-64-7
Chemical Structure| 1323290-64-7
Structure of 1323290-64-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1323290-64-7 ]

CAS No. :1323290-64-7 MDL No. :MFCD29917025
Formula : C6H13ClN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CFJYPWQHBLMCCU-UHFFFAOYSA-N
M.W :196.63 g/mol Pubchem ID :74765323
Synonyms :

Calculated chemistry of [ 1323290-64-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.82
TPSA : 95.41 Ų

Pharmacokinetics

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) : -8.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.75
Log Po/w (WLOGP) : -0.45
Log Po/w (MLOGP) : -0.64
Log Po/w (SILICOS-IT) : -0.92
Consensus Log Po/w : -0.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.26
Solubility : 109.0 mg/ml ; 0.554 mol/l
Class : Very soluble
Log S (Ali) : -0.78
Solubility : 32.9 mg/ml ; 0.167 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.03
Solubility : 182.0 mg/ml ; 0.925 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 1323290-64-7 ]

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:

Application In Synthesis of [ 1323290-64-7 ]

* 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 [ 1323290-64-7 ]

[ 1323290-64-7 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 1323407-17-5 ]
  • [ 1323290-64-7 ]
  • [ 1323407-19-7 ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 40℃; for 24h; 6.1.4 6.1.4
4-Carbamoyl-butyric acid methyl ester 6.1.4 4-Carbamoyl-butyric acid methyl ester To a stirred solution of methyl 2-(bromomethyl)-3-(tert-butyldimethylsilyloxy)benzoate (137.5 g, 325 mmol) in acetonitrile (1100 mL) in a 2 L round bottom flask, was added methyl 4,5-diamino-5-oxopentanoate hydrochloride (70.4 g, 358 mmol). To the suspension was added DIPEA (119 ml, 683 mmol) through an addition funnel over 10 minutes and the suspension was stirred at room temperature for 1 hour before the mixture was heated in an oil bath at 40° C. for 23 hours. The reaction mixture was concentrated under vacuo. The residue was stirred in ether (600 mL), and a white solid precipitated out. The mixture was filtered and the solid was washed with ether (400 mL). The filtrate was washed with HCl (1N, 200 mL), NaHCO3 (sat. 200 mL) and brine (250 mL). The aqueous acid layer and basic layer were kept separately. Then the solid was further washed with ether (250 mL) and the liquid was washed with above acid solution and basic solution. The two organic layers were combined and concentrated under vacuo to give 4-[4-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester as a brown oil (152 g, 115% crude yield, 77% purity by H NMR). The compound was used in the next step without further purification: LCMS MH=407.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 40℃; for 24.16h; 1.4 4-Carbamoyl-butyric acid methyl ester To a stirred solution of methyl 2-(bromomethyl)-3-(tert-butyldimethylsilyloxy)benzoate (137.5 g, 325 mmol) in acetonitrile (1100 mL) in a 2 L round bottom flask, was added methyl 4,5-diamino-5-oxopentanoate hydrochloride (70.4 g, 358 mmol). To the suspension was added DIPEA (119 ml, 683 mmol) through an addition funnel over 10 minutes and the suspension was stirred at room temperature for 1 hour before the mixture was heated in an oil bath at 40° C. for 23 hours. The reaction mixture was concentrated under vacuo. The residue was stirred in ether (600 mL), and a white solid precipitated out. The mixture was filtered and the solid was washed with ether (400 mL). The filtrate was washed with HCl (1N, 200 mL), NaHCO3 (sat. 200 mL) and brine (250 mL). The aqueous acid layer and basic layer were kept separately. Then the solid was further washed with ether (250 mL) and the liquid was washed with above acid solution and basic solution. The two organic layers were combined and concentrated under vacuo to give 4-[4-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester as a brown oil (152 g, 115% crude yield, 77% purity by 1H NMR). The compound was used in the next step without further purification: LCMS MH=407.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 40℃; for 24h; 6.4 4-Carbamoyl-butyric acid methyl ester To a stirred cold solution of methyl 5-amino-4-(4-(tert-butyldimethylsilyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (152 g, 288 mmol) in DMF (500 mL) and water (55 mL), was added by K2CO3 (19.89 g, 144 mmol) by portions over 5 minutes. The resulting reaction mixture was stirred at room temperature for 40 minutes. The reaction mixture was cooled in an ice bath. To the mixture, HCl (12M, 23.99 ml, 288 mmol) was added slowly. After the addition, acetonitrile (280 mL) was added to the mixture and a solid precipitated out. The mixture was stirred at room temperature for 10 minutes and filtered. The solid was washed with acetonitrile (50 mL x 4). The filtrate was concentrated under high vacuo to give a yellow oil (168 g). The oil was dissolved in acetonitrile (600 mL) and stirred at room temperature for 10minutes. The mixture was filtered and the solid was washed with acetonitrile (25 mL x 2). The filtrate was concentrated under high vacuo to give a yellow oil (169g), which was added to a mixture of water (1200 mL) and ether (1000 mL). The mixture was stirred for 3 minutes and the layers were separated. The aqueous solution was concentrated under high vacuo and the residue was stirred in acetonitrile (160 mL) and a white solid was formed after overnight stirring. The mixture was filtered to give 4- carbamoyl-4-(4-hydroxy-1-oxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester as a white solid (46 g, 54% yield). The filtrate was concentrated and the residue was further crystallized in acetonitrile (60 mL) to give more 4-carbamoyl-4-(4-hydroxy-1-oxo-1,3- dihydro-isoindol-2-yl)-butyric acid methyl ester as a white solid( 11.7 g, 14% yield). The filtrate was concentrated and the residue was purified by ISCO chromatography to give more 4-carbamoyl-4-(4-hydroxy-1-oxo-1,3-dihydro-isoindol -2-yl)-butyric acid methyl ester as a white solid (13.2 g, 15% yield). The total product obtained was 70.9 g in 83% yield: LCMS MH = 293; 1H NMR (DMSO-d6) δ 1.95 - 2.34 (m, 4H, CH2, CH2), 3.51 (s, 3H, CH3), 4.32 (d, J= 17.6 Hz, 1H, CHH), 4.49 (d, J= 17.4 Hz, 1H, CHH), 4.73 (dd, J = 4.7, 10.2 Hz, 1H, CHH), 6.99 (dd, J= 0.8, 7.9 Hz, 1H, Ar), 7.10 - 7.23 (m, 2H, Ar, NHH), 7.25 - 7.38 (m, 1H, Ar), 7.58 (s, 1H, NHH), 10.04 (s, 1H, OH).
In acetonitrile at 0 - 50℃; for 5h;
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; 1 Methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-1-oxo-isoindolin-2-yl]-5-oxo-pentanoate To a stirred solution of methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (74.5 g, 379 mmol) in acetonitrile (2.50 L) was added methyl 2-(bromomethyl)-3-[tert-butyl(dimethyl)silyl] oxy-benzoate (125 g, 348 mmol). To the suspension was added diisopropylethylamine (89.9 g, 696 mmol) through an addition funnel over 10 min and then the mixture was stirred at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate (1.0 L), washed with HCl (1N, 1.0 L), sodium bicarbonate (sat. 1.0 L) and brine (1.0 L) successively. The organic layer was concentrated to give crude methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-1-oxo-isoindolin-2-yl]-5-oxo-pentanoate (108 g, crude) as a light yellow solid. LCMS: m/z 407.3 [M+1]+.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16.166h; 1 Methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-l-oxoisoindolin-2- yl]-5-oxo-pentanoate. To a stirred solution of methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (74.5 g, 379 mmol) in acetonitrile (2.50 L) was added methyl 2- (bromomethyl)-3-[tert-butyl(dimethyl)silyl] oxy-benzoate (125 g, 348 mmol). To the suspension was added diisopropylethylamine (89.9 g, 696 mmol) through an addition funnel over 10 min and then the mixture was stirred at 60 °C for 16 h. The reaction mixture was diluted with ethyl acetate (1.0 L), washed with HC1 (IN, 1.0 L), sodium bicarbonate (sat.1.0 L) and brine (1.0 L) successively. The organic layer was concentrated to give crude methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-l-oxo- isoindolin-2-yl]- 5-oxo-pentanoate (108 g, crude) as a light yellow solid. LCMS: m/z 407.3 [M+l]+.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; 1 Methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-1-oxo-isoindolin-2-yl]-5-oxo-pentanoate Methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-1-oxo-isoindolin-2-yl]-5-oxo-pentanoate To a stirred solution of methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (74.5 g, 379 mmol) in acetonitrile (2.50 L) was added methyl 2-(bromomethyl)-3-[tert-butyl(dimethyl)silyl]oxy-benzoate (125 g, 348 mmol). To the suspension was added diisopropylethylamine (89.9 g, 696 mmol) through an addition funnel over 10 min and then the mixture was stirred at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate (1.0 L), washed with HCl (1N, 1.0 L), sodium bicarbonate (sat. 1.0 L) and brine (1.0 L) successively. The organic layer was concentrated to give crude methyl 5-amino-4-[4-[tert-butyl(dimethyl)silyl]oxy-1-oxo-isoindolin-2-yl]-5-oxo-pentanoate (108 g, crude) as a light yellow solid. LCMS: m/z 407.3 [M+1]+.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 23h; 6.1.4 (4) 4-Carbamoyl-butyric acid methyl ester To a stirred solution of methyl 2-(bromomethyl)-3-(tert - butyldimethylsilyloxy )benzoate (137.5 g, 325 mmol) in acetonitrile (1100 mL) in a 2 L round bottom flask, was added methyl 4,5-diamino-5-oxopentanoate hydrochloride (70.4 g, 358 mmol). To the suspension was added DIPEA (119 ml, 683 mmol) through an addition funnel over 10 minutes and the suspension was stirred at room temperature for 1 hour before the mixture was heated in an oil bath at 40°C for 23 hours. The reaction mixture was concentrated under vacuo. The residue was stirred in ether (600 mL), and a white solid precipitated out. The mixture was filtered and the solid was washed with ether (400 mL). The filtrate was washed with HC1 (IN, 200 mL), NaHCOs (sat. 200 mL) and brine (250 mL). The aqueous acid layer and basic layer were kept separately. Then the solid was further washed with ether (250 mL) and the liquid was washed with above acid solution and basic solution. The two organic layers were combined and concentrated under vacuo to give 4-[4- (tert -Butyl-dimethyl-silanyloxy)-l-oxo-l,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester as a brown oil (152g, 115% crude yield, 77% purity by H NMR). The compound was used in the next step without further purification: LCMS MH = 407.
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 23h; 6.1.4 (4) 4-Carbamoyl-butyric acid methyl ester To a stirred solution of methyl 2-(bromomethyl)-3-(tert - butyldimethylsilyloxy )benzoate (137.5 g, 325 mmol) in acetonitrile (1100 mL) in a 2 L round bottom flask, was added methyl 4,5-diamino-5-oxopentanoate hydrochloride (70.4 g, 358 mmol). To the suspension was added DIPEA (119 ml, 683 mmol) through an addition funnel over 10 minutes and the suspension was stirred at room temperature for 1 hour before the mixture was heated in an oil bath at 40°C for 23 hours. The reaction mixture was concentrated under vacuo. The residue was stirred in ether (600 mL), and a white solid precipitated out. The mixture was filtered and the solid was washed with ether (400 mL). The filtrate was washed with HC1 (IN, 200 mL), NaHCOs (sat. 200 mL) and brine (250 mL). The aqueous acid layer and basic layer were kept separately. Then the solid was further washed with ether (250 mL) and the liquid was washed with above acid solution and basic solution. The two organic layers were combined and concentrated under vacuo to give 4-[4- (tert -Butyl-dimethyl-silanyloxy)-l-oxo-l,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester as a brown oil (152g, 115% crude yield, 77% purity by H NMR). The compound was used in the next step without further purification: LCMS MH = 407.

Reference: [1]Hansen, Joshua D.; Correa, Matthew; Nagy, Mark A.; Alexander, Matt; Plantevin, Veronique; Grant, Virginia; Whitefield, Brandon; Huang, Dehua; Kercher, Timothy; Harris, Roy; Narla, Rama Krishna; Leisten, Jim; Tang, Yang; Moghaddam, Mehran; Ebinger, Katalin; Piccotti, Joseph; Havens, Courtney G.; Cathers, Brian; Carmichael, James; Daniel, Thomas; Vessey, Rupert; Hamann, Lawrence G.; Leftheris, Katerina; Mendy, Derek; Baculi, Frans; Lebrun, Laurie A.; Khambatta, Gody; Lopez-Girona, Antonia [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 6648 - 6676]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2014/45843, 2014, A1 Location in patent: Paragraph 0417
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2014/45844, 2014, A1 Location in patent: Paragraph 0287; 0288
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2014/39960, 2014, A1 Location in patent: Page/Page column 62
[5]Current Patent Assignee: ARVINAS - WO2018/140809, 2018, A1 Location in patent: Paragraph 00393
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2019/8852, 2019, A1 Location in patent: Paragraph 0112; 0316
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/226761, 2019, A1 Location in patent: Paragraph 00275; 00282
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2019/361005, 2019, A1 Location in patent: Paragraph 1068
[9]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2022/72576, 2022, A1 Location in patent: Paragraph 00291
[10]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2022/72576, 2022, A1 Location in patent: Paragraph 00291
  • 2
  • [ 1323290-64-7 ]
  • [ 1323407-16-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2: potassium carbonate; water / N,N-dimethyl-formamide / 15 h / 15 °C
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere
  • 3
  • [ 1323290-64-7 ]
  • [ 1323407-22-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C 3: potassium carbonate / acetonitrile / 16 h / 60 °C
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2: potassium carbonate; water / N,N-dimethyl-formamide / 15 h / 15 °C 3: potassium carbonate / acetonitrile / 16 h / 60 °C
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere
  • 4
  • [ 1323290-64-7 ]
  • [ 1323407-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -70 °C 4.2: -70 - 20 °C
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2.1: potassium carbonate; water / N,N-dimethyl-formamide / 15 h / 15 °C 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -70 °C 4.2: -70 °C
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice
  • 5
  • [ 1323290-64-7 ]
  • [ 1323404-89-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: sulfuric acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
  • 6
  • [ 1323290-64-7 ]
  • [ 1323410-28-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: acetonitrile / 20 °C / Inert atmosphere
  • 7
  • [ 1323290-64-7 ]
  • [ 1323405-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 8
  • [ 1323290-64-7 ]
  • [ 1323405-76-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 9
  • [ 1323290-64-7 ]
  • [ 1323406-46-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C / Inert atmosphere
  • 10
  • [ 1323290-64-7 ]
  • [ 1323406-54-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C / Inert atmosphere
  • 11
  • [ 1822563-16-5 ]
  • [ 1323290-64-7 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In ethyl acetate at 25℃; for 12h; 1 Methyl 4,5-diamino-5-oxo-pentanoate hydrochloride A mixture of methyl 5-amino-4-(tert-butoxycarbonylamino)-5-oxo-pentanoate (180 g, 692 mmol) and HCl/ethyl acetate (300 mL, 4 M) was stirred at 25° C. for 12 h. The precipitated solid was collected by vacuum filtration and washed with ethyl acetate (500 mL) to give methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (130 g, 95% yield) as a white solid. 1H NMR: 400 MHz CD3OD δ: 4.00-3.96 (m, 1H), 3.70 (s, 3H), 2.59-2.52 (m, 2H), 2.22-2.13 (m, 2H).
95% With hydrogenchloride In ethyl acetate at 25℃; for 12h; 1 Methyl 4, 5-diamino- 5-oxo-pentanoate hydrochloride A mixture of methyl 5-amino-4-(tert-butoxycarbonylamino)-5-oxo-pentanoate (180 g, 692 mmol) and HCl/ethyl acetate (300 mL, 4 M) was stirred at 25 °C for 12 h. The precipitated solid was collected by vacuum filtration and washed with ethyl acetate (500 mL) to give methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (130 g, 95 % yield) as a white solid. (0496) ^ NMR: 400 MHz CD3OD d: 4.00-3.96 (m, 1H), 3.70 (s, 3H), 2.59-2.52 (m, 2H), 2.22-2.13 (m, 2H).
95% With hydrogenchloride In ethyl acetate at 25℃; for 12h; 1 Methyl 4,5-diamino-5-oxo-pentanoate hydrochloride Methyl 4,5-diamino-5-oxo-pentanoate hydrochloride A mixture of methyl 5-amino-4-(tert-butoxycarbonylamino)-5-oxo-pentanoate (180 g, 692 mmol) and HCl/ethyl acetate (300 mL, 4 M) was stirred at 25° C. for 12 h. The precipitated solid was collected by vacuum filtration and washed with ethyl acetate (500 mL) to give methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (130 g, 95% yield) as a white solid. 1H NMR: 400 MHz CD3OD δ: 4.00-3.96 (m, 1H), 3.70 (s, 3H), 2.59-2.52 (m, 2H), 2.22-2.13 (m, 2H).
95% With hydrogenchloride In ethyl acetate at 25℃; for 12h; Inert atmosphere;

  • 12
  • [ 1323290-64-7 ]
  • [ 2260745-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -70 °C 4.2: -70 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2.1: potassium carbonate; water / N,N-dimethyl-formamide / 15 h / 15 °C 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -70 °C 4.2: -70 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C / Inert atmosphere
  • 13
  • [ 14487-45-7 ]
  • [ 1323290-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / methanol / 2 h / 25 °C 2.1: pyridine; di-<i>tert</i>-butyl dicarbonate / 1,4-dioxane / 0.5 h / 25 °C 2.2: 16 h / 25 °C 3.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 3 steps 1.1: triethylamine / methanol / 2 h / 25 °C 2.1: pyridine / 1,4-dioxane / 0.5 h / 25 °C 2.2: 16 h / 25 °C 3.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 3 steps 1.1: triethylamine / 2 h / 25 °C / Inert atmosphere 2.1: di-<i>tert</i>-butyl dicarbonate; pyridine / 1,4-dioxane / 0.5 h / 25 °C / Inert atmosphere 2.2: 16 h / 25 °C / Inert atmosphere 3.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C / Inert atmosphere
  • 14
  • [ 617-65-2 ]
  • [ 1323290-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane / methanol / 0.5 h / 20 °C / Inert atmosphere 2.1: triethylamine / methanol / 2 h / 25 °C 3.1: pyridine; di-<i>tert</i>-butyl dicarbonate / 1,4-dioxane / 0.5 h / 25 °C 3.2: 16 h / 25 °C 4.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane / 0.5 h / 20 °C / Inert atmosphere 2.1: triethylamine / methanol / 2 h / 25 °C 3.1: pyridine / 1,4-dioxane / 0.5 h / 25 °C 3.2: 16 h / 25 °C 4.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane / 0.5 h / 20 °C / Inert atmosphere 2.1: triethylamine / 2 h / 25 °C / Inert atmosphere 3.1: di-<i>tert</i>-butyl dicarbonate; pyridine / 1,4-dioxane / 0.5 h / 25 °C / Inert atmosphere 3.2: 16 h / 25 °C / Inert atmosphere 4.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C / Inert atmosphere
  • 15
  • [ 112159-16-7 ]
  • methyl 4,5-diamino-5-oxo-pentanoate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine; di-<i>tert</i>-butyl dicarbonate / 1,4-dioxane / 0.5 h / 25 °C 1.2: 16 h / 25 °C 2.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 2 steps 1.1: pyridine / 1,4-dioxane / 0.5 h / 25 °C 1.2: 16 h / 25 °C 2.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C
Multi-step reaction with 2 steps 1.1: di-<i>tert</i>-butyl dicarbonate; pyridine / 1,4-dioxane / 0.5 h / 25 °C / Inert atmosphere 1.2: 16 h / 25 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 12 h / 25 °C / Inert atmosphere
  • 16
  • [ 1323290-64-7 ]
  • [ 2260745-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -70 °C 4.2: -70 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C
  • 17
  • [ 1323290-64-7 ]
  • [ 2586195-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: sulfuric acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 0 - 15 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / -5 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere
  • 18
  • [ 1323290-64-7 ]
  • [ 2586194-31-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: sulfuric acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 0 - 15 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / -5 °C / Inert atmosphere
  • 19
  • [ 1323290-64-7 ]
  • [ 2586195-75-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere
  • 20
  • [ 1323290-64-7 ]
  • [ 2586194-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere
  • 21
  • [ 1323290-64-7 ]
  • [ 2586196-41-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere
  • 22
  • [ 1323290-64-7 ]
  • [ 2586196-46-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere
  • 23
  • [ 1323290-64-7 ]
  • [ 2586196-39-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere
  • 24
  • [ 1323290-64-7 ]
  • [ 2586195-79-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere
  • 25
  • [ 1323290-64-7 ]
  • [ 2586194-99-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 60 °C / Inert atmosphere
  • 26
  • [ 1323290-64-7 ]
  • [ 2586195-81-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; potassium carbonate / 4 h / 25 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 12 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere
  • 27
  • [ 1323290-64-7 ]
  • [ 1323407-39-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / 0 °C / Inert atmosphere
  • 28
  • [ 1323290-64-7 ]
  • [ 1323411-23-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 29
  • [ 1323290-64-7 ]
  • [ 2586197-43-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 30
  • [ 1323290-64-7 ]
  • [ 2699881-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 31
  • [ 1323290-64-7 ]
  • [ 2586196-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 32
  • [ 1323290-64-7 ]
  • [ 2586197-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 33
  • [ 1323290-64-7 ]
  • [ 2722673-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C / Inert atmosphere 6.1: hydrogenchloride / methanol / Inert atmosphere
  • 34
  • [ 1323290-64-7 ]
  • [ 2586196-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
  • 35
  • [ 1323290-64-7 ]
  • [ 1323405-54-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: acetonitrile / 20 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
  • 36
  • [ 1323290-64-7 ]
  • [ 2586194-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 60 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 40 °C / Inert atmosphere
  • 37
  • [ 1323290-64-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / 0 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / Inert atmosphere; Cooling with ice
  • 38
  • [ 1323290-64-7 ]
  • [ 1323410-26-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere 2.2: 0.17 h / 20 °C / Inert atmosphere 3.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / 0 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Inert atmosphere
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