(R)-2-amino-N-benzyl-3-methoxypropanamide supplier

Name
(R)-2-amino-N-benzyl-3-methoxypropanamide
EINECS 606-353-2
CAS No. 196601-69-1
Article Data38
CAS DataBase
Density 1.107 g/cm³
Solubility
Melting Point
Formula C₁₁H₁₆N₂O₂
Boiling Point 421.947 °C at 760 mmHg
Molecular Weight 208.26
Flash Point 208.986 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2(R)-Amino-N-benzyl-3-methoxypropionamide;
PSA 64.35000
LogP 1.36770

Synthetic route

: 196601-68-0
(R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 3h; Ambient temperature;	100%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 4h;	96%
With palladium 10% on activated carbon; hydrogen at 20℃;	95%

: 880468-89-3
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With hydrogenchloride; water In dichloromethane at 0 - 30℃; for 2h;	100%
With hydrogenchloride; water In dichloromethane at 0 - 30℃; for 2h;	100%
With hydrogenchloride In dichloromethane; water at 0 - 10℃; for 1h;	100%

: C17H19N3O4

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Stage #1: C17H19N3O4 With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 4h; Stage #2: With [bis(acetoxy)iodo]benzene In acetonitrile at 0℃; for 0.5h; Stage #3: With sulfuric acid at 20℃; for 1h; enantioselective reaction;	95%

: 1253790-58-7
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate

: 77-78-1
dimethyl sulfate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Stage #1: tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate; dimethyl sulfate With water; sodium hydroxide; tetrabutylammomium bromide In dichloromethane at -10 - -5℃; Stage #2: With hydrogenchloride In dichloromethane; water at 25 - 30℃; for 2h;	90.71%

: 262845-82-9
N-Benzyl-2-Amino-3-Methoxypropionamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With L-Tartaric acid; phosphoric acid; benzaldehyde In methanol at 50℃; pH=6;	72%

: 100-46-9
benzylamine

N-acetyl-N'-(3,4-dichlorophenylhaloacetyl)-hydrazide: N-acetyl-N'-(3,4-dichlorophenylhaloacetyl)-hydrazide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 4-methylmorpholine / tetrahydrofuran / 0.03 h / -78 °C 1.2: isobutyl chloroformate / tetrahydrofuran / 0.03 h 1.3: 65 percent / tetrahydrofuran / -78 - 20 °C 2.1: 90 percent / Ag2O / acetonitrile / 20 °C 3.1: 96 percent / H2 / Pd/C / methanol / 4 h / 20 °C / 760 Torr View Scheme

: 219835-31-1
(R)-N-benzyl 2-N-(benzyloxycarbonyl)amino-3-hydroxypropionamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Ag2O / acetonitrile / 20 °C 2: 96 percent / H2 / Pd/C / methanol / 4 h / 20 °C / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: 84 percent / Ag2O / acetonitrile / 72 h / Ambient temperature 2: 100 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: silver(l) oxide / acetonitrile / 120 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / water; tert-butyl methyl ether / 12 h / -10 - 5 °C 2.1: hydrogenchloride; water / 0.75 h / 40 - 45 °C 2.2: 0 - 5 °C View Scheme

: 100-46-9
benzylamine

chloride of/the/ 2-nitro-toluene-sulfonic acid-(4): chloride of/the/ 2-nitro-toluene-sulfonic acid-(4)

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h / Ambient temperature 2: 84 percent / Ag2O / acetonitrile / 72 h / Ambient temperature 3: 100 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme

: 1159573-88-2
N-benzyl-O-methyl-N2-trityl-D-serinamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Stage #1: N-benzyl-O-methyl-N2-trityl-D-serinamide With hydrogenchloride In dichloromethane; water at 20℃; for 0.5h; Stage #2: With ammonia In water
Stage #1: N-benzyl-O-methyl-N2-trityl-D-serinamide With acetic acid In ethanol at 20℃; for 0.5h; Stage #2: With ammonia In water Product distribution / selectivity;
With hydrogenchloride In dichloromethane; water at 20℃; for 0.5h; Product distribution / selectivity;

: C20H24N2O4

: 196601-68-0
(R)-N-benzyl 2-N-(benzylcarboxycarbonyl)amino-3-methoxypropionamide

A: C12H18N2O2

B: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 30 - 35℃; under 3750.38 - 4500.45 Torr; for 1h;

...Expand

: (R)-N-benzyl-2-amino-3-methoxypropionamide oxalate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With sodium hydroxide In water

: 100-46-9
benzylamine

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / -5 °C 1.2: -5 - 0 °C 2.1: potassium hydroxide / dichloromethane / 5 °C 2.2: 5 °C 3.1: hydrogenchloride / dichloromethane; water / 25 - 30 °C 3.2: 25 - 30 °C / pH 10 - 11 View Scheme
Multi-step reaction with 3 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate / 3.5 h / 4 - 25 °C / Inert atmosphere 2.1: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water / 4 - 25 °C / Inert atmosphere 3.1: hydrogenchloride; water / dichloromethane / 3 h / 25 °C 3.2: 4 - 8 °C View Scheme
Multi-step reaction with 3 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate / 3.5 h / 4 - 25 °C / Cooling with ice; Inert atmosphere 2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane; water / 4 - 25 °C / Cooling with ice; Inert atmosphere 3.1: hydrogenchloride; water / dichloromethane / 3 h / 25 °C 3.2: 4 - 8 °C View Scheme

: 1253790-58-7
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / dichloromethane / 5 °C 1.2: 5 °C 2.1: hydrogenchloride / dichloromethane; water / 25 - 30 °C 2.2: 25 - 30 °C / pH 10 - 11 View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water / 4 - 25 °C / Inert atmosphere 2.1: hydrogenchloride; water / dichloromethane / 3 h / 25 °C 2.2: 4 - 8 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane; water / 4 - 25 °C / Cooling with ice; Inert atmosphere 2.1: hydrogenchloride; water / dichloromethane / 3 h / 25 °C 2.2: 4 - 8 °C View Scheme

: 1346691-15-3
(R)-N-benzyl-2-(dibenzylamino)-3-methoxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With hydrogen; palladium(II) hydroxide In methanol at 25 - 30℃; under 3677.86 Torr; for 8h; Inert atmosphere;
With hydrogen; palladium(II) hydroxide In methanol at 25 - 30℃; under 3750.38 Torr; for 8h; Inert atmosphere;

: 175481-39-7
(2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ethyl acetate / 1 h / 25 - 30 °C 1.2: 1 h / 25 - 30 °C 2.1: sodium hydroxide; water / tetrabutylammomium bromide / dichloromethane / -10 - -5 °C 2.2: 2 h / 25 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran 2.1: potassium hydroxide; tetrabutylammomium bromide / ethyl acetate 3.1: hydrogenchloride / water / Reflux 3.2: pH 8 - 9 View Scheme
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran 2: tetrabutylammomium bromide; potassium hydroxide / ethyl acetate 3: hydrogenchloride; water / Reflux View Scheme

: 1357171-71-1
(2R)-2-azido-N-benzyl-3-hydroxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 1 h / 25 - 30 °C / 2795.17 Torr / Autoclave 2.1: ethyl acetate / 1 h / 25 - 30 °C 2.2: 1 h / 25 - 30 °C 3.1: sodium hydroxide; water / tetrabutylammomium bromide / dichloromethane / -10 - -5 °C 3.2: 2 h / 25 - 30 °C View Scheme

: 1357171-70-0
(2S)-N-benzyl-2-bromo-3-hydroxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium azide / N,N-dimethyl-formamide / 50 - 55 °C 2.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 1 h / 25 - 30 °C / 2795.17 Torr / Autoclave 3.1: ethyl acetate / 1 h / 25 - 30 °C 3.2: 1 h / 25 - 30 °C 4.1: sodium hydroxide; water / tetrabutylammomium bromide / dichloromethane / -10 - -5 °C 4.2: 2 h / 25 - 30 °C View Scheme

: 1320360-91-5
(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / ethyl acetate 2.1: hydrogenchloride / water / Reflux 2.2: pH 8 - 9 View Scheme
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / ethyl acetate 2: hydrogenchloride; water / Reflux View Scheme

: 1320360-92-6
(R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Stage #1: (R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide With hydrogenchloride In water Reflux; Stage #2: With sodium hydroxide In water pH=8 - 9;
With hydrogenchloride; water Reflux;

: 1322062-75-8
(2R)-2-amino-N-benzyl-3-hydroxypropanamide hydrochloride

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / water / 20 - 25 °C / pH 8 - 9 2: triethylamine / tetrahydrofuran 3: tetrabutylammomium bromide; potassium hydroxide / ethyl acetate 4: hydrogenchloride; water / Reflux View Scheme

: N-benzyl-2-amino-3-methoxypropanamide N-formyl-L-leucine salt

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With alkaline salt solution In dichloromethane; water	1.59 g

: (R)-tert-butyl (1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)-N-(hydroxymethyl)carbamate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tert-butyl methyl ether / 60 - 65 °C 2: hydrogenchloride; water / dichloromethane / 2 h / 0 - 30 °C View Scheme

: (R)-N-benzyl-2-(isoindolin-2-yl)-3-methoxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With hydrazine hydrate In isopropyl alcohol at 0 - 25℃; for 2h; Inert atmosphere;
With hydrazine hydrate In isopropyl alcohol at 0 - 25℃; for 2h; Inert atmosphere;

: C10H12ClNO2

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol / 3 h / 0 - 20 °C / Inert atmosphere 2: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 3: sodium azide / water; N,N-dimethyl-formamide / 6 h / 70 °C / Inert atmosphere 4: 5%-palladium/activated carbon; hydrogen / methanol / 3 h / 20 °C / Autoclave View Scheme

: 1567820-75-0
(S)-N-benzyl-2-hydroxy-3-methoxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2: sodium azide / water; N,N-dimethyl-formamide / 6 h / 70 °C / Inert atmosphere 3: 5%-palladium/activated carbon; hydrogen / methanol / 3 h / 20 °C / Autoclave View Scheme

: 1567820-77-2
(S)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl 4-toluenesulfonate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / water; N,N-dimethyl-formamide / 6 h / 70 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / methanol / 3 h / 20 °C / Autoclave View Scheme

: (R)-2-azido-N-benzyl-3-methoxypropanamide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 3h; Autoclave;

: 86118-11-8
D-o-methylserine

: 100-46-9
benzylamine

A: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

B: 474534-78-6
(S)-N-benzyl 2-amino-3-methoxypropionamide

Conditions

Conditions	Yield
With tris(2,2,2-trifluoroethyl) borate at 125℃; under 760.051 Torr; for 4h;	A n/a B n/a

...Expand

: 108-24-7
acetic anhydride

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: lacosamide

Conditions

Conditions	Yield
With pyridine; dmap In tetrahydrofuran for 1h; Ambient temperature;	90%
With pyridine In tetrahydrofuran at 20℃; for 1h; enantioselective reaction;	88%
at 10 - 25℃;	81.8%

: 598-21-0
2-Bromoacetyl bromide

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: N-benzyl-2-(2-bromo-acetylamino)-3-methoxy-propionamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate In dichloromethane at 5 - 10℃;	78%

: 108-22-5
Isopropenyl acetate

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: lacosamide

Conditions

Conditions	Yield
In Isopropyl acetate at 23 - 75℃;	68.9%

: 75-36-5
acetyl chloride

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: lacosamide

Conditions

Conditions	Yield
With triethylamine at 10 - 25℃;	62.4%
With triethylamine In dichloromethane at 10 - 25℃;	3.12 g
With sodium carbonate In toluene at 0 - 5℃; for 1h; Inert atmosphere;	935 mg
With sodium carbonate In toluene at 0 - 5℃; for 1h;	935 mg
With triethylamine at 0 - 20℃; for 1.58333h; Inert atmosphere;	108 mg

: 75-07-0
acetaldehyde

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: N-benzyl-2-ethylamino-3-methoxy-propionamide

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol at 20℃; for 0.166667h;	51%

: 108-24-7
acetic anhydride

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

A: (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide

B: lacosamide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;

...Expand

: C12H18N2O2

: 108-24-7
acetic anhydride

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

A: C14H20N2O3

B: lacosamide

Conditions

Conditions	Yield
With triethylamine In ethyl acetate at 20℃; for 1h;

...Expand

: 144-62-7
oxalic acid

: 196601-69-1
(R)-2-amino-N-benzyl-3-methoxypropanamide

: (R)-N-benzyl-2-amino-3-methoxypropionamide oxalate

Conditions

Conditions	Yield
In isopropyl alcohol at 0 - 32℃; for 1.25h;

(R)-2-amino-N-benzyl-3-methoxypropanamide Specification

The (R)-2-amino-N-benzyl-3-methoxypropanamide, with the cas registry number 196601-69-1, has the systematic name of N-benzyl-O-methyl-D-serinamide and IUPAC name of 2-amino-N-benzyl-3-methoxypropanamide. This is a kind of white to off-white crystalline powder and this chemica is usually applied as the organic intermediate.

The characteristics of this chemical are as follows: (1)ACD/LogP: 0.86; (2)ACD/LogD (pH 7.4): 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 2; (5)ACD/KOC (pH 5.5): 12; (6)ACD/KOC (pH 7.4): 55; (7)#H bond acceptors: 4; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 64.35; (11)Index of Refraction: 1.535; (12)Molar Refractivity: 58.564 cm³; (13)Molar Volume: 188.123 cm³; (14)Polarizability: 23.217×10^-24 cm³; (15)Surface Tension: 43.213 dyne/cm; (16)Density: 1.107 g/cm³; (17)Flash Point: 208.986 °C; (18)Enthalpy of Vaporization: 67.604 kJ/mol; (19)Boiling Point: 421.947 °C at 760 mmHg; (20)Exact Mass: 208.121178; (21)MonoIsotopic Mass: 208.121178; (22)Topological Polar Surface Area: 64.4; (23)Heavy Atom Count: 15; (24)Formal Charge: 0; (25)Complexity: 191.

Additionally, the following datas could be converted into the molecular structure:
(1)SMILES:O=C(NCc1ccccc1)[C@H](N)CO
(2)InChI:InChI=1/C11H16N2O2/c1-15-8-10(12)11(14)13-7-9-5-3-2-4-6-9/h2-6,10H,7-8,12H2,1H3,(H,13,14)/t10-/m1/s1
(3)InChIKey:WPLANNRKFDHEKD-SNVBAGLBBS

Product Name

(R)-2-amino-N-benzyl-3-methoxypropanamide

Synthetic route

(R)-2-amino-N-benzyl-3-methoxypropanamide Specification

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