BOC-L-Isoleucine Chemical Properties

Melting point:

66-69 °C(lit.)

alpha 

2 º (c=2,CH3COOH)

Boiling point:

373.37°C (rough estimate)

Density 

1.1202 (rough estimate)

refractive index 

2.7 ° (C=2, AcOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetic Acid, DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.03±0.22(Predicted)

color 

White to Off-White

optical activity

[α]20/D +2.7°, c = 2 in acetic acid

Water Solubility 

Soluble in methanol. Insoluble in water.

BRN 

1711700

CAS DataBase Reference

13139-16-7(CAS DataBase Reference)

EPA Substance Registry System

L-Isoleucine, N-[(1,1-dimethylethoxy)carbonyl]- (13139-16-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29241990

MSDS

• Language:English Provider:BOC-L-Isoleucine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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BOC-L-Isoleucine Usage And Synthesis

Chemical Properties

white fine crystalline powder

Uses

N-Boc-L-isoleucine is used to prepare BOC-L-isoleucine hydroxysuccinimide ester by using 1-hydroxybenzotriazole and 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride.

reaction suitability

reaction type: Boc solid-phase peptide synthesis
reaction type: C-H Activation
reagent type: ligand
reaction type: Peptide Synthesis

Synthesis

GENERAL STEPS: L-isoleucine (1.31 g, 10 mmol, 1.0 equiv) was dissolved in 20.5 mL of 1 M NaOH solution and cooled in an ice bath. Di-tert-butyl dicarbonate (Boc2O, 2.62 g, 12 mmol, 1.2 equiv) dissolved in 7 mL of dioxane was added slowly. The reaction mixture was stirred at ambient temperature for 24 hours. Subsequently, the pH of the reaction solution was adjusted to 10 with 1 M NaOH and ether was added for phase separation. The aqueous phase was acidified to pH 2 with 1 M HCl and extracted with ethyl acetate (EtOAc). The combined organic phases were washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give BOC-L-isoleucine as a colorless oil (2.20 g, 95% yield). IR (cm-1): 3292 (w), 2967 (m), 2934 (w), 2880 (w), 1713 (s), 1661 (m), 1504 (m), 1465 (w), 1394 (m), 1368 (s), 1242 (m), 1159 (s), 1121 (m), 1046 (m), 1019 (w), 857 (w), 778 857 (w), 778 (w), 657 (w). 1H NMR (500 MHz, CDCl3) δ: 0.94 (t, J = 7.3 Hz, 3H, H-6), 0.98 (d, J = 7 Hz, 3H, H-4), 1.15-1.29 (m, 1H, H-5a), 1.46 (s, 9H, H-9/10/11), 1.46-1.54 (m, partially overlapped, 1H, H-5b), 1.83-1.99 (m, 1H, H-3), 4.30 (dd, J = 8.9, 4.6 Hz, 1H, H-2), 5.02 (d, J = 8.9 Hz, 1H, NH). 13C NMR (125 MHz, CDCl3) δ: 11.8 (C-6), 15.7 (C-4), 25.0 (C-5), 28.5 (C-9/10/11), 37.9 (C-3), 58.0 (C-2), 80.2 (C-8), 155.9 (C-7), 177.2 (C-1). HRMS (ESI) m/z: [M-H]- calcd for C11H20NO4 230.13868, found 230.13926. [α]20D +3.6 (c 2.00, CH3OH) (Lit [3]: [α]25D +3.8 (c 1.01, CH3OH)).

References

[1] Tetrahedron Letters, 2005, vol. 46, # 38, p. 6537 - 6540
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3573 - 3586
[4] Tetrahedron, 1992, vol. 48, # 37, p. 8007 - 8022
[5] Tetrahedron, 2006, vol. 62, # 31, p. 7274 - 7283

BOC-L-Isoleucine (13139-16-7)Related Product Information

• (2R,3R)-2-Amino-3-methylpentanoic acid
• 1,1'-Carbonyldiimidazole
• tert-Butyl acetate
• L-Isoleucine
• tert-Butyl peroxyacetate
• DL-Isoleucine
• N-CARBOBENZOXY-DL-LEUCINE
• tert-Butanol
• CARBONYL SULFIDE
• Boc-L-Cyclopentylglycine
• (S)-TERT-BUTOXYCARBONYLAMINO-INDAN-1-YL-ACETIC ACID
• NICKEL CARBONYL
• Boc-N-Methyl-L-isoleucine
• Boc-L-Cyclohexylglycine
• BOC-ALLO-ISOLEUCINE
• BOC-D-ISOLEUCINE extrapure,N-T-BOC-D-ISOLEUCINE,N-ALPHA-T-BOC-D-ISOLEUCINE,BOC-D-ISOLEUCINE
• Boc-L-isoleucine amide
• L-Isovaline