| Identification | More | [Name]
Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate | [CAS]
3392-05-0 | [Synonyms]
BOC-D-ALANINE-HYDROXYSUCCINIMIDE ESTER
BOC-D-ALANINE N-HYDROXYSUCCINIMIDE ESTER
BOC-D-ALANINE-OSU
BOC-D-ALA-OSU
N-ALPHA-T-BOC-D-ALANINE N-HYDROXYSUCCINIMIDE ESTER
succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
Boc-L-Alanine N-hydroxysuccinimde ester
BOC-L-ALA-OSU
Boc-L-alanineydroxysuccinimidester
Boc-Ala-OSu
Boc-L-alanine N-succinimidyl ester
BOC-ALANINE-1-HYDROXYSUCCINIMIDE ESTER
BOC-L-ALANINE-HYDROXYSUCCINIMIDESTER
N-(tert-butoxycarbonyl)-L-alanine hydroxysuccinimide ester
Boc-L-alanine N-succinimidyl ester, Boc-L-alanine hydroxysuccinimide ester
(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]propionic acid 2,5-dioxopyrrolidin-1-yl ester
[(S)-1-[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]ethyl]carbamic acid 1,1-dimethylethyl ester
N-(tert-Butoxycarbonyl)alanine 2,5-dioxopyrrolizino
N-(tert-Butoxycarbonyl)-L-alanine 2,5-dioxopyrrolizino
N-(tert-Butyloxycarbonyl)-L-alanine 2,5-dioxopyrrolizino | [EINECS(EC#)]
222-229-7 | [Molecular Formula]
C12H18N2O6 | [MDL Number]
MFCD00037907 | [Molecular Weight]
286.28 | [MOL File]
3392-05-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
161-163 °C | [alpha ]
-52 º (c=2.5% in dioxane) | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in water or 1% acetic acid | [form ]
Powder | [pka]
10.81±0.46(Predicted) | [Appearance]
White to off-white Solid | [Optical Rotation]
[α]20/D 52±3.5°, c = 2.5% in dioxane | [Sensitive ]
Moisture Sensitive | [BRN ]
3560476 | [Major Application]
peptide synthesis | [InChI]
1S/C12H18N2O6/c1-7(13-11(18)19-12(2,3)4)10(17)20-14-8(15)5-6-9(14)16/h7H,5-6H2,1-4H3,(H,13,18)/t7-/m0/s1 | [InChIKey]
COMUWNFVTWKSDT-ZETCQYMHSA-N | [SMILES]
C[C@H](NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O | [CAS DataBase Reference]
3392-05-0(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
| [F ]
3-10-21 | [HS Code ]
29224999 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
Reactant involved in synthesis of:
- Muramyldipeptide analogs via solid-phase synthesis
- Microcin C analogs for use as antibacterials
- Lipid I and nucleoside diphosphate peptide derivatives via N-methylimidazolium chloride catalyzed coupling
- N-Protected dipeptide acids
- Free and peptide-bound glycated amino acids for studies of interactions with human Caco-2 interstinal epithelial cell apical membrane transport proteins
- 7-Substituted camptothecin conjugates with RGD-peptides as avβ3 integrin ligands
| [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Example 11: Preparation of N-succinimidyl N-tert-butoxycarbonyl-L-alanine ester
0.95 g (5 mmol) of N-tert-butoxycarbonyl-L-alanine and 0.66 ml (5.5 mmol) of N-methylmorpholine were dissolved in 6 ml of tetrahydrofuran (THF), followed by a one-time addition of 1.8 g (5.5 mmol) of N-succinimidyl 1,2,2,2-tetrachloroethyl carbonate. The reaction mixture was stirred at 20°C for 2 hours. After completion of the reaction, it was diluted by adding about 25 ml of ethyl acetate, and the organic phase was washed quickly with 1N HCl solution, potassium bicarbonate solution in sequence, and finally washed twice with water. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized by ethyl acetate/petroleum ether mixed solvent to give 1.25 g (87% yield) of white crystals. Evaporation of the mother liquor and recrystallization recovered 0.1 g of product, raising the overall yield to 94%. The melting point of the product was 158 °C. [α]D20 = +50.7 (c = 2, dioxane). | [References]
[1] Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2364 - 2367
[2] Patent: US4782164, 1988, A |
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