2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
- CAS NO.：851784-82-2
- Empirical Formula: C15H17Cl2NO4
- Molecular Weight: 346.21
- MDL number: MFCD22370640
- Update Date: 2025-09-28 17:38:58
What is 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid?
Description
2-(tert-Butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic Acid is a carboxylic acid derivative of tetrahydroisoquinoline with a Boc group and two chlorine atoms attached to the tetrahydroisoquinoline ring. It may exhibit various biological activities, such as anticancer, anti-inflammatory, and anticonvulsant properties, depending on the nature and position of the substituents.
The Uses of 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
2-(tert-Butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic Acid is a reagent in the preparation of N-benzofuranylcarbonyl dichlorotetrahydroisoquinolinylcarbonylmethylsulfonyl L-phenylalanine as LFA-1 inhibitor and polymorph thereof for the treatment of LFA -1 mediated diseases.
Synthesis
Boc-protection was used for the ring nitrogen in the intermediates 21 and 22.Compound 5 was deprotected with HC1 in dioxane to produce compound 23 in better than 97%yield. Boc-protection was introduced, using di-tert-butyl dicarbonate (1 .1 equivalent), and compound 21 was obtained in better than 95% yield. Compound 10 was coupled with compound 21 to obtain compound 22, using HATU and triethylamine in DMF. The product, compound 22, was obtained in quantitative yield, and greater than 90% purity. Deprotection with HC1 yielded the compound of Formula 12 in 97.4% yield.
Properties of 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
| Boiling point: | 468.5±45.0 °C(Predicted) |
| Density | 1.379±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Sparingly, Sonicated), Methanol (Slightly) |
| form | Solid |
| pka | 1.87±0.20(Predicted) |
| color | White to Off-White |
| InChI | InChI=1S/C15H17Cl2NO4/c1-15(2,3)22-14(21)18-5-4-9-8(7-18)6-10(16)11(12(9)17)13(19)20/h6H,4-5,7H2,1-3H3,(H,19,20) |
Safety information for 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
| InChIKey | JXBQRXIJBFUZMR-UHFFFAOYSA-N |
| SMILES | C1C2=C(C(Cl)=C(C(O)=O)C(Cl)=C2)CCN1C(OC(C)(C)C)=O |
2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid manufacturer
ALS India Life Sciences Pvt. Ltd
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