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| | (S)-N-Boc-3-Bromophenylalanine Basic information |
| | (S)-N-Boc-3-Bromophenylalanine Chemical Properties |
| Melting point | 106.1°C | | Boiling point | 475.3±40.0 °C(Predicted) | | density | 1.5311 (rough estimate) | | refractive index | 1.6500 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | pka | 3.81±0.10(Predicted) | | form | Solid | | color | White to off-white | | Optical Rotation | Consistent with structure | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 | | InChIKey | FBUDYESOPLBQIR-NSHDSACASA-N | | SMILES | C(O)(=O)[C@H](CC1=CC=CC(Br)=C1)NC(OC(C)(C)C)=O | | CAS DataBase Reference | 82278-73-7(CAS DataBase Reference) |
| HazardClass | IRRITANT | | HS Code | 2922498590 |
| | (S)-N-Boc-3-Bromophenylalanine Usage And Synthesis |
| Chemical Properties | off-white powder | | Uses | N-Boc-3-bromo-L-phenylalanine is used as pharmaceutical intermediate. | | Synthesis | The general procedure for the synthesis of (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid from di-tert-butyl dicarbonate and (S)-2-amino-3-(3-bromophenyl)propionic acid was as follows: first, the reaction was carried out using sodium bicarbonate (3 eq.) and di-tert-butyl dicarbonate (Boc2O, 1.1 eq.) on the (S)-2-amino-3-(3-bromophenyl)propionic acid in a mixed solvent of dioxane and water. -(3-bromophenyl)propionic acid by tert-butoxycarbonyl (Boc) protection reaction to afford the Boc-protected intermediate 7 in 98% yield.Subsequently, the reaction was carried out in dimethylsulfoxide (DMSO) with cuprous iodide (0.4 eq.), cesium carbonate (0.5 eq.), L-proline (0.8 eq.), and sodium salt of methanesulfinic acid (3.9 eq.) as catalysts at 95-100 °C for 9 hours, during which two additional additions of cuprous iodide (0.2 eq.) and L-proline (0.4 eq.) were made, converting the brominated intermediate 7 to the methylsulfoxide-functionalized product 8 in 96% yield. Next, the carboxylic acid group of compound 8 was esterified to a benzyl ester using benzyl alcohol (1.1 eq.), 4-dimethylaminopyridine (DMAP, 0.1 eq.) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC, 1.0 eq.) to give compound 9 in 99% yield. Finally, a Boc deprotection reaction of the amino group was carried out by adding a dioxane solution of 4N HCl to a dichloromethane solution of compound 9 at 0 °C to give the target product 10 in the form of the HCl salt of the free amino group in 94% yield. | | References | [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1. Location in patent: Paragraph 00120; 00121; 00122; 00123; 00124; 00125
[3] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
[4] Patent: WO2009/102876, 2009, A1. Location in patent: Page/Page column 56 |
| | (S)-N-Boc-3-Bromophenylalanine Preparation Products And Raw materials |
| Raw materials | 3-Bromo-L-phenylalanine-->Benzenepropanamide, α-amino-3-bromo-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl--->Di-tert-butyl dicarbonate-->1,4-Dioxane-->Water-->Sodium bicarbonate | | Preparation Products | L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1)-->benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate-->L-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester-->N-Boc-3-bromo-L-phenylalanine ethyl ester |
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