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

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

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

2(R)-Amino-N-benzyl-3-methoxypropionamide;

Article Data 38

(R)-2-amino-N-benzyl-3-methoxypropanamide 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 30 - 35℃; under 3750.38 - 4500.45 Torr; for 1h;

(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
 

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