| Identification | More | [Name]
(3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID | [CAS]
79261-58-8 | [Synonyms]
(3S)-2-[BENZYLOXYCARBONYL]-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
N-ALPHA-CARBOBENZOXY-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
(S)-(+)-2-(BENZYLOXYCARBONYL)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID
(S)-(+)-N-CBZ-1,2,3,4-TERTRAHYDRO ISOQUINOLINE-3-CARBOXYLIC ACID
Z-[3S]-1,2,3,4-TETRAHYDROISOQUINOLENE-3-CARBOXYLIC ACID
Z-D-[3S]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
Z-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
Z-TIC-OH
(S)-(+)-2-(BENZYLOXYCARBONYL)-TETRAHY-DR O-3-ISOQUINOLINECARBOXYLIC ACID, 97%
(S)-N-Benzyloxycarbonyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid | [Molecular Formula]
C18H17NO4 | [MDL Number]
MFCD00672545 | [Molecular Weight]
311.33 | [MOL File]
79261-58-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [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. ]
Store at 0-5°C | [form ]
Solid | [pka]
3.86±0.20(Predicted) | [color ]
White to pale yellow | [CAS DataBase Reference]
79261-58-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [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 |
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