| Identification | Back Directory | [Name]
2-(TERT-BUTOXYCARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-6-CARBOXYLIC ACID | [CAS]
170097-67-3 | [Synonyms]
Lifitegrast Impurity 45
N-BOC-6-HYDROXYCARBONYL-1,2,3,4-TETRAHYDRO
N-Boc-1,2,3,4-tetrahydroisoquinoline-6-carboxylic
2-Boc-1,2,3,4-Tetrahydroisoquinoline-6-Carboxylic Acid
N-BOC-6-HYDROXYCARBONYL-1,2,3,4-TETRAHYDROISOQUINOLINE
N-BOC-1,2,3,4-TETRAHYDROISOQUINOLINE-6-CARBOXYLIC ACID
2-(Tert-Butoxycarbonyl)-1,2,3,4-Tetrahydroisoquinoline-6-Car...
3,4-DIHYDRO-1H-ISOQUINOLINE-2,6-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER
2-(TERT-BUTOXYCARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-6-CARBONIC ACID
2-(TERT-BUTOXYCARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-6-CARBOXYLIC ACID
2,6(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) ester
2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-6-carboxylic acid | [Molecular Formula]
C15H19NO4 | [MDL Number]
MFCD05861548 | [MOL File]
170097-67-3.mol | [Molecular Weight]
277.32 |
| Chemical Properties | Back Directory | [Boiling point ]
429.3±45.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
4.33±0.20(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
N-Boc-1,2,3,4-Tetrahydroisoquinoline-6-carboxylic Acid is the starting material used to prepare benzazole derivatives as β-secretase inhibitors useful in treatment and prevention of diseases. | [Synthesis]
Step 2: Synthesis of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid; To a mixture of methanol/tetrahydrofuran (1:1, 6 mL) of the crude urethane obtained from Step 1 was added 1N sodium hydroxide solution (1.97 mL, 1.97 mmol). The reaction mixture was heated to 70 °C and maintained for 1 hour. After the reaction was completed, the mixture was cooled and methanol was removed by rotary evaporator. The remaining aqueous solution was acidified to pH 4 with 1 N hydrochloric acid.The resulting precipitate was collected by vacuum filtration and dried to give the target product (0.34 g, 93% yield), which could be used in subsequent reactions without further purification. Mass spectrum (electrospray positive ion mode) m/e 222.0 [M-tBu]+. | [References]
[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5167 - 5182
[2] Patent: WO2009/49154, 2009, A1. Location in patent: Page/Page column 40
[3] Patent: EP3192791, 2017, A1. Location in patent: Paragraph 0596
[4] European Journal of Medicinal Chemistry, 2019, p. 317 - 333
[5] Patent: WO2006/114313, 2006, A1. Location in patent: Page/Page column 159 |
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