Structure of Boc-DL-Nva-OH
CAS No.: 521286-38-4
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CAS No. : | 521286-38-4 |
Formula : | C10H19NO4 |
M.W : | 217.26 |
SMILES Code : | CCCC(C(O)=O)NC(OC(C)(C)C)=O |
MDL No. : | MFCD00270725 |
InChI Key : | INWOAUUPYIXDHN-UHFFFAOYSA-N |
Pubchem ID : | 302433 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (CAS 102185-35-3, 500 mg, 2.16 mmol) in DCM (5 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (497 mg, 2.59 mmol) and stirred for 10 minutes at rt. A solution of N,O-dimethylhydroxylamine hydrochloride (253 mg, 2.59 mmol) and DIPEA (0.429 mL, 2.59 mmol) in DCM (5 mL) was added and the reaction mixture was left to stir at rt over weekend. The mixture was diluted with DCM (30 mL) and extracted with saturated aqueous NaHCO3 (50 mL). The organic phase was washed with water before being dried over MgSO4 and evaporated to give the title compound (466 mg, 79%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A mixture of 2-tert-butoxycarbonylamino-pentanoic acid (1.0 eq.), 2-amino-5-methyl thiazole (1.0 eq. ), HOBt (1.05 eq. ), EDC. HCI (1.2 eq. ) and a triethylamine (4 eq. ) in methylene chloride was stirred at room temperature overnight. The mixture was quenched with water and extracted with methylene chloride. The organic layer was washed with diluted HCI, separated, dried over sodium sulfate and filtered. The solvent was removed at reduced pressure to provide product. [M+1=314. 3, 1H] NMR (DMSO-d6) d 7.11 (s, 1H), 4.11 (m, 1H), 2.3 (s, 3H), 1.54 (m, 2H), 1.34 (t, 9H), 1.2-1. 4 (m, 2H), 0.83 (t, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A mixture of 2-tert-butoxycarbonylamino-pentanoic acid (5.432g, 25 mmol.), 5-tert-butyl-[1,3,4]thiadiazol-2-ylamine (3.925g, 25 mmol), HBOT (3.540g, 26.25 mmol), EDC HCl (5.73g, 30 mmol.) and triethylamine (14 ml) in methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound (9.2671 g), LC-MS M+1=357.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; | t-Butoxycarbonylaminovaleric acid 5-Aminovaleric acid was converted under Schotten-Baumann conditions with di-t-butyl carbonate in the usual manner into the corresponding N-protected acid, melting point 48-50 (from ether/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.2% | With ammonium bicarbonate; In N,N-dimethyl-formamide; at 20℃; | General procedure: DL-N-Boc-2-aminobutyric acid was dissolved in DMF,and NH4HCO3and CH3Iwere added at room temperature.The mixture was stirred for 12 h in room temperature. Thereaction solution (compound b) was extracted with ethyl acetate,and then washed with saturated sodium chloride solution(50mL × 3), dried over anhydrous sodium sulfate and concentratedunder vacuum [13] (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydrogencarbonate; In methanol; water; at 20℃; | General procedure: An amino acid (1.0 eq.), Boc anhydride (1.5 eq.), and sodium bicarbonate (1.5 eq.) were dissolved in a mixedsolvent of distilled water and methanol (1:1), and allowed to react at room temperature for 36 to 48 hours. After completionof the reaction, the resultant was washed twice with diethyl ether, and then the pH of the water layer was adjusted to 2with 1.0 M hydrochloric acid. Then, extraction with ethyl acetate (EA) was performed. The obtained organic layer wasdehydrated using a desiccant (sodium sulfate) and dried under reduced pressure, to obtain the desired compound, anamino acid of which an amine group had been protected with a protecting group (Boc). |