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| | 4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Basic information |
| | 4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Chemical Properties |
| Melting point | 164-168 °C | | Boiling point | 427.8±38.0 °C(Predicted) | | density | 1.178±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 4.25±0.10(Predicted) | | form | Crystalline | | color | Off-white | | BRN | 2854286 | | Major Application | peptide synthesis | | InChI | 1S/C13H17NO4/c1-13(2,3)18-12(17)14-8-9-4-6-10(7-5-9)11(15)16/h4-7H,8H2,1-3H3,(H,14,17)(H,15,16) | | InChIKey | LNKHBRDWRIIROP-UHFFFAOYSA-N | | SMILES | CC(C)(C)OC(=O)NCc1ccc(cc1)C(O)=O | | CAS DataBase Reference | 33233-67-9(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 22-26-36/37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29242990 | | Storage Class | 11 - Combustible Solids |
| | 4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Usage And Synthesis |
| Chemical Properties | white solid | | Uses | 4-(Boc-aminomethyl)benzoic Acid is the Boc protected form of 4-(Aminomethyl)benzoic Acid (A615230) and is used as a reagent in the synthesis of indoleamide derivatives as EP2 antagonists with high selectivity. 4-(Boc-aminomethyl)benzoic Acid is also used as a reagent in the synthesis of aminopyridine-derived amides as nicotinamide phosphoribosyltransferase inhibitors. | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | Phase 1 - Boc Protection: 4-(Aminomethyl)benzoic acid (10.00 g, 65.36 mmol) was stirred with di-tert-butyl dicarbonate (28.0 g, 130.72 mmol) in a solvent mixture of deionized water (100 mL) and tetrahydrofuran (100 mL) at room temperature. The reaction system was adjusted to pH ≈ 6 by slow addition of saturated aqueous sodium bicarbonate solution and the reaction was continuously stirred for 16 hours. Upon completion of the reaction, the reaction solution was carefully acidified to pH ≈ 3 with 1 M hydrochloric acid solution, at which time a white solid precipitated. The solid product was collected by filtration and washed with deionized water and dried to afford 4-[(tert-butoxycarbonylamino)methyl]benzoic acid as a white solid (16.1 g, 97% yield). Mass spectrometry analysis showed m/z = 274 [M + Na]+. | | References | [1] Patent: WO2008/53131, 2008, A1. Location in patent: Page/Page column 58; 59-60
[2] Patent: WO2008/40934, 2008, A1. Location in patent: Page/Page column 57-58
[3] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 206
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 965 - 984
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 501 - 508 |
| | 4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Preparation Products And Raw materials |
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