BOC-TIC-OH Chemical Properties

Melting point:

125-126.5 °C

Boiling point:

420.18°C (rough estimate)

Density 

1.1311 (rough estimate)

refractive index 

1.5080 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

soluble in Methanol

form 

Solid

pka

3.88±0.20(Predicted)

color 

White to off-white

optical activity

[α]20/D +19.0±1.5°, c = 0.7% in methanol

BRN 

4297114

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

BOC-TIC-OH Usage And Synthesis

Chemical Properties

white to light beige powder

Uses

Boc-Tic-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Synthesis

The general procedure for the synthesis of (R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from di-tert-butyl dicarbonate and (S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was as follows: (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (50.0 g, 282 mmol) was suspended in 1,4-dioxane ( 1000 mL) and water (500 mL) in a solvent mixture with vigorous stirring. Sodium bicarbonate (47.4 g, 564 mmol) and di-tert-butyl dicarbonate (67.7 g, 310 mmol) were subsequently added and the reaction mixture was stirred continuously at room temperature for 6 days. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was dissolved in water (2000 mL). A 30% w/v aqueous solution of sodium bisulfate monohydrate (300 mL) was added and extracted with chloroform (3 x 1000 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the target product (R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (90.0 g, quantitative yield) as a thick slurry.Results of LCMS analysis: retention time 3.64 min; mass spectrometry data m/z 178.1 [M-Boc + 2H]+ ; m/ z 276.1 [M-H]-.

References

[1] Patent: WO2017/153513, 2017, A1. Location in patent: Page/Page column 78
[2] Patent: WO2017/153515, 2017, A1. Location in patent: Page/Page column 62
[3] Patent: WO2017/153520, 2017, A1. Location in patent: Page/Page column 44; 47
[4] Patent: WO2017/153519, 2017, A1. Location in patent: Page/Page column 56; 59
[5] Tetrahedron Letters, 2001, vol. 42, # 43, p. 7559 - 7561

BOC-TIC-OH(78879-20-6)Related Product Information

• BOC-L-TYROSINE ETHYL ESTER
• Boc-L-serine methyl ester
• Boc-L-Tyrosine methyl ester
• BOC-VAL-NH2
• BOC-SER-OH
• N-Boc-L-tert-Leucine
• N-Boc-L-valine
• BOC-L-TYR-OL
• BOC-TRP-OME
• Boc-L-Threonine
• BOC-L-Tyrosine
• O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-serine tert-Butyl Ester
• 5,6,7,8-TETRAHYDROISOQUINOLINE
• L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
• 1,2,3,4-TETRAHYDROISOQUINOLINE
• H-TIC-OH