| Identification | More | [Name]
Boc-Asp-OtBu | [CAS]
34582-32-6 | [Synonyms]
BOC-ASPARTIC ACID-OTBU
BOC-ASP-OBUT
BOC-ASP-OTBU
BOC-L-ASPARTIC ACID ALPHA-BUTYL ESTER
BOC-L-ASPARTIC ACID ALPHA-T-BUTYL ESTER
BOC-L-ASP-OTBU
N-ALPHA-T-BOC-L-ASPARTIC ACID ALPHA-T-BUTYL ESTER
N-ALPHA-T-BUTOXYCARBONYL-L-ASPARTIC ACID ALPHA-T-BUTYL ESTER
N-ALPHA-T-BUTYLOXYCARBONYL-L-ASPARTIC ACID-ALPHA-T-BUTYL ESTER
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-ASPARTIC ACID-ALPHA-TERT-BUTYL ESTER
N-tert-Butoxycarbonyl-L-aspartic acid tert-butyl ester
NALPHA-tert-Butoxycarbonyl-L-aspartic acid ALPHA-tert-butyl ester
Boc-L-Aspartic acid 1-tert-butyl ester
N-tert-Butyloxycarbonyl-L-aspartic acid 1-tert-butyl ester
(S)-2-(tert-Butoxycarbonylamino)succinic acid 4-tert-butyl ester
N-(tert-Butoxycarbonyl)aspartic acid 4-tert-butyl ester
N-(tert-Butoxycarbonyl)-L-aspartic acid 4-tert-butyl ester
N-(tert-Butyloxycarbonyl)-L-aspartic acid 4-tert-butyl ester
N-[[(tert-Butyl)oxy]carbonyl]-L-aspartic acid 4-(tert-butyl) ester
(2S)-2-(tert-Butoxycarbonylamino)succinic acid 1-tert-butyl ester | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C13H23NO6 | [MDL Number]
MFCD00038272 | [Molecular Weight]
289.32 | [MOL File]
34582-32-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
101-103?C | [Boiling point ]
429.0±40.0 °C(Predicted) | [density ]
1.139 | [storage temp. ]
-15°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
4.13±0.19(Predicted) | [color ]
White | [Optical Rotation]
[α]/D -24.5±1.5°, c = 1 in methanol | [BRN ]
4191701 | [InChI]
InChI=1S/C13H23NO6/c1-12(2,3)19-10(17)8(7-9(15)16)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,15,16)/t8-/m0/s1 | [InChIKey]
RAUQRYTYJIYLTF-QMMMGPOBSA-N | [SMILES]
C(OC(C)(C)C)(=O)[C@H](CC(O)=O)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
34582-32-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
An aspartic acid derivative, Boc-Asp-OtBu can be used in stereoselective synthesis
| [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of N-tert-butoxycarbonyl-L-aspartic acid 1-tert-butyl ester from (S)-2-(BOC-amino) succinic acid (4-benzyl) ester (1-tert-butyl): (S)-2-(BOC-amino) succinic acid (4-benzyl) ester (1-tert-butyl) ester (1.04 g, 2.74 mmol) was reacted with 10% Pd/C (0.2 g) in a The mixture in anhydrous ethanol (20 mL) was placed under hydrogen atmosphere (50 psi) and the reaction was shaken for 3 hours. Upon completion of the reaction, the mixture was filtered and the filtrate was concentrated under vacuum to give a white crystalline solid N-tert-butyl N-tert-butoxycarbonyl-L-aspartate 1- tert-butyl ester (0.79 g, 100%). The product has a melting point of 97-99 °C (literature value 1: 97-98 °C; literature value 2: 98-100 °C); specific rotation [α]24D = -16.9 (c = 1.0, EtOH) and [α]23D = -23.6 (c = 1.5, MeOH) (literature 2: [α]22D = +19.6 (c = 1.0, CHCl3); literature 3: [α] 25D = -7.4 (c = 2.0, MeOH)).1H NMR (200 MHz, CDCl3) δ 10.33 (br s, 1H), 5.48 (d, 1H, J = 8.0 Hz), 4.45 (t, 1H, J = 4.0 Hz), 3.02 (dd, 1H, J1 = 17.0 Hz, J2 = 4.0 Hz), 2.81 ( dd, 1H, J1 = 11 Hz, J2 = 4.6 Hz), 1.45 (br s, 18H); 13C NMR (50 MHz, CDCl3) δ 175.8, 169.9, 155.7, 82.4, 80.2, 50.5, 36.8, 28.3, 27.9; High-resolution mass spectrometry (HRMS) calculations C13H23NaNO6(M + Na)+: 312.1423, measured value: 312.1420. references: 1. C. C. Yang, R. B. Merrifield. Journal of Organic Chemistry 1976, 41, 1032-1041; 2. Robert M. Adlington, Jack E. Baldwin, David Catterick, Gareth J. Pareth, J. Pritchard. J. Chem. Soc., Perkin Trans. 1, 1999, 855-866. | [References]
[1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 8, p. 855 - 866
[2] Tetrahedron, 2001, vol. 57, # 30, p. 6557 - 6566
[3] Patent: WO2011/20018, 2011, A1. Location in patent: Page/Page column 23
[4] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 1122 - 1133
[5] Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2369 - 2376 |
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