| Identification | Back Directory | [Name]
(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate | [CAS]
880468-89-3 | [Synonyms]
LacosaMide interMediate
Lacosamide impurity A CRS
-tert-Butyl 1-(benzylamino)
-3-methoxy-1-oxopropan-2-ylcarbamate
(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxoprop
(R)-2-tert-butyryl amino-benzylyl-3-methoxypropamide
(R)-2-tert-butoxycarbonylamino-N-benzyl-3-methoxypropionamide
(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcar...
tert-butyl N-[(1R)-1-(benzylcarbaMoyl)-2-Methoxyethyl]carbaMate
(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate
tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate
O-methyl-N-alpha-[phenylmethoxy]carbonyl]-N-(phenylmethyl)-D-Serinamide
tert -Butyl [(2R)-1 -(benzylamino)-3-methoxy-1 -oxopropan-2-yl]carbamate
Tert-butyl of (R) 1- (butylamino) -3-methoxy-1-oxypropane-2-yl carbamate
tert-butyl N-[(1R)-2-(benzylamino)-1-(methoxymethyl)-2-oxo-ethyl]carbamate
N-[3-methoxy-1-oxo-1-[(phenylmethyl)amino]propan-2-yl]carbamic acid tert-butyl ester
Carbamic acid, N-[(1R)-1-(methoxymethyl)-2-oxo-2-[(phenylmethyl)amino]ethyl]-, 1,1-dimethylethyl ester
Carbamic acid,[(1R)-1-(methoxymethyl)-2-oxo-2-[(phenylmethyl)amino]ethyl]-, 1,1-dimethylethylester (9CI) | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C16H24N2O4 | [MDL Number]
MFCD16620517 | [MOL File]
880468-89-3.mol | [Molecular Weight]
308.37 |
| Chemical Properties | Back Directory | [Melting point ]
63-64 °C | [Boiling point ]
507.6±50.0 °C(Predicted) | [density ]
1.103±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
10.62±0.46(Predicted) | [color ]
White to Off-White | [InChI]
1S/C16H24N2O4/c1-16(2,3)22-15(20)18-13(11-21-4)14(19)17-10-12-8-6-5-7-9-12/h5-9,13H,10-11H2,1-4H3,(H,17,19)(H,18,20)/t13-/m1/s1 | [InChIKey]
ZEWWJSJMNBJIKR-CYBMUJFWSA-N | [SMILES]
N([C@H](COC)C(=O)NCc1ccccc1)C(=O)OC(C)(C)C |
| Hazard Information | Back Directory | [Uses]
(R)-tert-Butyl 1-(Benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate is an intermediate in the synthesis of functionalized amino acids, and in the synthesis of antiepileptic drug (R)-lacosamide. | [Synthesis]
The general procedure for the synthesis of (R)-2-tert-butoxycarbonylamino-N-benzyl-3-methoxypropanamide from tert-butyl (R)-(1-(phenylmethylamino)-3-hydroxy-1-oxopropan-2-yl)carbamate and dimethyl sulfate was as follows: toluene (4.8 L) was added to a reactor at room temperature, followed by the addition of the Lacosamide Phase II product (1 kg) , and the mixture was cooled to 0°C. Sodium hydroxide solution (0.54 kg), tetrabutylammonium bromide (0.186 kg) and dimethyl sulfate (0.86 kg) were added sequentially, and then the reaction mixture was heated to 30°C with continuous stirring for 90 minutes. After completion of the reaction, the organic phase was separated by extraction with toluene and washed by adding 5% sodium bicarbonate solution. Cyclohexane was added to the organic phase and stirred for 10 minutes, followed by concentration under reduced pressure at 50°C for 2 hours. Finally, the product was dried to give lacosamide III in about 96.28% yield. | [References]
[1] Patent: CN106957239, 2017, A. Location in patent: Paragraph 0036; 0045-0047
[2] Patent: EP2399901, 2011, A1. Location in patent: Page/Page column 8
[3] Patent: US2011/319649, 2011, A1. Location in patent: Page/Page column 5
[4] Patent: US2011/34731, 2011, A1. Location in patent: Page/Page column 7
[5] Patent: WO2011/144983, 2011, A2. Location in patent: Page/Page column 26-27 |
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