| Identification | More | [Name]
N-Cbz-L-Aspartic acid 4-tert-butyl ester | [CAS]
5545-52-8 | [Synonyms]
CBZ-L-ASPARTIC ACID 4-TERT-BUTYL ESTER
N-BENZYLOXYCARBONYL-L-ASPARTIC ACID 4-TERT-BUTYL ESTER
N-CBZ-L-ASPARTIC ACID 4-TERT-BUTYL ESTER
Z-ASPARTIC ACID(OTBU)-OH
Z-ASP(OTBU)-OH
Z-L-ASPARTIC ACID 4-TERT-BUTYL ESTER
Z-L-ASP(OTBU)-OH
4-tert-butyl hydrogen N-[(phenylmethoxy)carbonyl]-L-aspartate
Cbz-Asp(OtBu)-OH
Z-L-aspartic acid β-tert·butyl ester monohydrate
N-CBZ-L-ASPARTIC ACID-B-T-BUTYL ESTER
ASP(OtBu)-OH
N-ALPHA-BENZYLOXYCARBONYL-L-ASPARTIC ACID BETA-TERT-BUTYL ESTER 1-HYDRATE
CBZ-ASP(OBUT)-OH
Z-Asp(OtBu)-OH.H20
Z-Aspartic acid, 4-tert-Butyl ester, H20
Z-L-ASPARTIC ACID-B-T BUTYLESTER MONOHYDRATE
CBZ-AMINOACID
CBZ-L-ASPARTIC ACID .BETA.-TERT-BUTYL ESTER MONOHYDRATE
N-Carbobenzyloxy-L-aspartic acid β-tert butyl ester | [EINECS(EC#)]
226-912-0 | [Molecular Formula]
C16H21NO6 | [MDL Number]
MFCD00042857 | [Molecular Weight]
323.34 | [MOL File]
5545-52-8.mol |
| Chemical Properties | Back Directory | [Boiling point ]
513.1±50.0 °C(Predicted) | [density ]
1.219±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO, and methanol. | [form ]
Powder | [pka]
3.67±0.23(Predicted) | [color ]
White to off-white | [Optical Rotation]
29°(C=0.01g/mL, CHCL3, 20°C, 589nm) | [BRN ]
2569846 | [InChI]
InChI=1S/C16H21NO6/c1-16(2,3)23-13(18)9-12(14(19)20)17-15(21)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1 | [InChIKey]
HLSLRFBLVZUVIE-LBPRGKRZSA-N | [SMILES]
C(O)(=O)[C@H](CC(OC(C)(C)C)=O)NC(OCC1=CC=CC=C1)=O | [CAS DataBase Reference]
5545-52-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29224999 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
It is a pharmaceutical intermediate. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of (S)-3-(((benzyloxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid, N-benzyloxycarbonyl-L-aspartic acid 4-tert-butyl ester and Z-L-aspartic acid tert-butyl ester tert-butyl ester, using tert-butyl acetate and N-CBZ-L-aspartic acid, is as follows: an ester-exchange reaction system was set up according to the methodology described in Example 1 , but BF3 -Et2O was replaced with other catalysts. The catalysts tested included acids or salts as listed in Table I. The reaction was carried out at room temperature or at about 50°C for 5.5 to 15 hours. At the end of the reaction, the reaction mixtures were analyzed by HPLC technique as in Example 1. The results of Table I show that the ester exchange reaction in the presence of catalysts such as concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2), and titanium tetrachloride in dichloromethane (TiCl4 in DCM), significantly produced Z-Asp(OtBu)2. In contrast, the catalytic effect of aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti[OiPr]4) was not significant even under the conditions of increasing the reaction temperature and prolonging the reaction time. | [References]
[1] Patent: US2003/236430, 2003, A1. Location in patent: Page 3
[2] Patent: US2003/236430, 2003, A1. Location in patent: Page 3
[3] Patent: US2003/236430, 2003, A1. Location in patent: Page 3
[4] Patent: US2003/236430, 2003, A1. Location in patent: Page 3
[5] Patent: US2003/236430, 2003, A1. Location in patent: Page 3 |
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