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Boc-Asp-OtBu

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Boc-Asp-OtBu Basic information
Product Name:Boc-Asp-OtBu
Synonyms:N-[[(tert-Butyl)oxy]carbonyl]-L-aspartic acid 4-(tert-butyl) ester;(2S)-2-(tert-Butoxycarbonylamino)succinic acid 1-tert-butyl ester;N-(tert-Butoxycarbonyl)-L-aspartic acid 1-tert-butyl ester;N-tert-Butoxycarbonyl-L-aspartic acid 1-tert-butyl ester;5-BOC-Asp-Ot Bu;N-Boc-L-aspartic acid 1-tert-butyl ester, 95%;(3s)-4-[(2-Methylpropan-2-yl)oxy]-3-[(2-Methylpropan-2-yl)oxycarbonylaMino]-4-oxobutanoic Acid;L-Asparticacid, N-[(1,1-diMethylethoxy)carbonyl]-, 1-(1,1-diMethylethyl) ester
CAS:34582-32-6
MF:C13H23NO6
MW:289.32
EINECS:1592732-453-0
Product Categories:Amino Acids & Derivatives;Chiral Reagents;Inhibitors;Amino Acid Derivatives;Aspartic acid [Asp, D];Boc-Amino Acids and Derivative
Mol File:34582-32-6.mol
Boc-Asp-OtBu Structure
Boc-Asp-OtBu Chemical Properties
Melting point 101-103C
Boiling point 429.0±40.0 °C(Predicted)
density 1.139
storage temp. Sealed in dry,2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka4.13±0.19(Predicted)
form Powder
color White
Optical Rotation[α]/D -24.5±1.5°, c = 1 in methanol
BRN 4191701
Major Applicationpeptide synthesis
InChIInChI=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
InChIKeyRAUQRYTYJIYLTF-QMMMGPOBSA-N
SMILESC(OC(C)(C)C)(=O)[C@H](CC(O)=O)NC(OC(C)(C)C)=O
CAS DataBase Reference34582-32-6(CAS DataBase Reference)
Safety Information
WGK Germany 3
HS Code 2924 19 00
Storage Class11 - Combustible Solids
MSDS Information
Boc-Asp-OtBu Usage And Synthesis
Chemical PropertiesWhite solid
UsesAn aspartic acid derivative, Boc-Asp-OtBu can be used in stereoselective synthesis
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
Synthesis
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester

80963-08-2

Boc-Asp-OtBu

34582-32-6

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
Tag:Boc-Asp-OtBu(34582-32-6) Related Product Information
3-(BOC-AMINO)-1-PROPANOL 1-Methyl L-aspartate N-Methyl-L-aspartic acid BOC-GLYCINE METHYL ESTER Boc-Asp-OtBu Glycine tert butyl ester hydrochloride L-Aspartic acid Boc-Asp-OH N-Formyl-L-aspartic acid N-Boc-L-Homoserine Mono-tert-butyl succinate (S)-(-)-2-(Boc-Amino)-1,4-butanediol H-ASP-OTBU BOC-ASP(OTBU)-OH BOC-ASP(OTBU)-OSU L-Aspartic acid 4-tert-butyl ester L-ASPARTIC ACID 4-tert-Butyl N-[(tert-butoxy)carbonyl]-L-aspartate dicyclohexylamine salt