| Identification | Back Directory | [Name]
N-boc Asp(OH)Ome | [CAS]
98045-03-5 | [Synonyms]
N-boc Asp(OH)Ome
1-Methyl N-Boc-L-aspartate
(Tert-Butoxy)Carbonyl Asp-OMe
Boc-L-aspartic acid 1-methyl ester
N-Boc-L-aspartic acid 1-Methyl ester, 98%
α-methyl N-(tert-butoxycarbonyl)aspartate
1-Methyl N-(tert-Butoxycarbonyl)-L-aspartate
N-tert-Butoxycarbonyla spartic acid a-methylester
N-tert-Butoxycarbonyl-L-aspartic acid 1-methyl ester
(S)-3-((tert-Butoxycarbonyl)amino)-4-methoxy-4-oxobutanoicacid
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl ester
(3S)-3-{[(tert-butoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid
N-[(1,1-Dimethylethoxy)carbonyl]-L-aspartic acid alpha-methyl ester | [Molecular Formula]
C10H17NO6 | [MDL Number]
MFCD03094777 | [MOL File]
98045-03-5.mol | [Molecular Weight]
247.25 |
| Chemical Properties | Back Directory | [Melting point ]
79-81℃ | [Boiling point ]
407.1±40.0 °C(Predicted) | [density ]
1.209 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Solid | [pka]
4.09±0.19(Predicted) | [color ]
White to Almost white |
| Hazard Information | Back Directory | [Uses]
N-Boc-L-aspartic acid 1-methyl ester is used as an intermediate in the preparation of modified alfa-amino acids and 5-cis-alkylprolines. | [Synthesis]
Boc-L-aspartyl (OBn)(OMe)14 (5.88 g, 17.43 mmol) was dissolved in methanol (20 mL) in a 50 mL round-bottomed flask and 10% palladium carbon catalyst was added under nitrogen protection. The reaction system was replaced three times with nitrogen and then three times with hydrogen. Subsequently, the reaction mixture was stirred under hydrogen atmosphere and atmospheric pressure for 6 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the target product (S)-3-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid (Compound 15) in the form of a colorless gel (4.1 g, 95% yield). The specific optical rotation [α]21D of the product was 34 (c 0.1, CHCl3).1H NMR (CDCl3, 400 MHz) δ: 1.43 (s, 9H), 2.83-2.86 (d, 1H, J = 16.92 Hz), 3.01-3.05 (d, 1H, J = 16.68 Hz), 3.74 (s, 3H), 4.57 (s , 1H), 5.55-5.57 (d, 1H, J = 8.12 Hz), 10.45 (s, 1H).13C NMR (CDCl3, 100 MHz) δ: 28.3, 36.6, 49.7, 52.8, 80.5, 155.5, 171.5, 176.0. IR (KBr) ν: 3366, 2980, 1719 , 1506, 1440, 1395, 1368, 1222, 1165, 1060, 1008, 864, 764, 587 cm-1. | [References]
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[2] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 15 - 20
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 586 - 590
[5] Carbohydrate Research, 2013, vol. 382, p. 36 - 42 |
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