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| | (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID Basic information |
| Product Name: | (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID | | Synonyms: | (S)-(+)-N-CBZ-1,2,3,4-TERTRAHYDRO ISOQUINOLINE-3-CARBOXYLIC ACID;N-ALPHA-CARBOBENZOXY-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;(3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;(3S)-2-CBZ-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;(S)-(+)-2-(BENZYLOXYCARBONYL)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID;(3S)-2-phenylmethoxycarbonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid;CBZ-L-7-HYDROXY-(3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;Z-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID | | CAS: | 79261-58-8 | | MF: | C18H17NO4 | | MW: | 311.33 | | EINECS: | | | Product Categories: | Building Blocks for HIV Protease InhibitorsChiral Building Blocks;Cell Signaling Enzymes;Heterocyclic Building Blocks;HIV Protease Reagents&Envelope Proteins;Isoquinolines | | Mol File: | 79261-58-8.mol |  |
| | (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID Chemical Properties |
| Melting point | 137-141 °C | | Boiling point | 451.38°C (rough estimate) | | density | 1.2626 (rough estimate) | | refractive index | 23.5 ° (C=2, MeOH) | | storage temp. | Sealed in dry,Room Temperature | | pka | 3.86±0.20(Predicted) | | form | Solid | | color | White to pale yellow | | CAS DataBase Reference | 79261-58-8(CAS DataBase Reference) |
| Provider | Language |
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ACROS
| English |
| | (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | (3S)-2-Carbobenzoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid is a reagent in the preparation of antibacterial studies of peptide deformylase inhibitor BB-3497 and its P2’ and P3’ analogs. | | Synthesis | General procedure for the synthesis of (S)-(+)-N-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from (S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and benzyl chloroformate: to an aqueous solution of 1 M NaOH (3.20 g, 80.0 mmol, dissolved in 80 mL of H2O) was added slowly at room temperature (S)-1 ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5.00 g, 28.2 mmol) and dioxane until the suspension was completely dissolved. Subsequently, benzyl chloroformate (6.25 g, 5.59 mL, 36.7 mmol) was added slowly and dropwise over 30 min at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. Dioxane was removed by evaporation and the reaction mixture was acidified with 1 M HCl to pH 2 at 0 °C. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to afford the target product, (S)-(+)-N-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (8.68 g, 27.9 mmol, 99% yield), as a white foamy solid without further purification. The product was characterized by 1H-NMR, 13C-NMR, MS and LC-MS to confirm its structure and purity. | | References | [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 2222 - 2243
[2] Patent: WO2017/63910, 2017, A1. Location in patent: Page/Page column 20-21
[3] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7575 - 7587
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4371 - 4373
[5] Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 956 - 968 |
| | (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID Preparation Products And Raw materials |
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