(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

form 

Solid

pka

3.86±0.20(Predicted)

color 

White to pale yellow

CAS DataBase Reference

79261-58-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36-36/37/39

HS Code 

29334900

MSDS

• Language:English Provider:ACROS

(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

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