| Identification | More | [Name]
BOC-L-Isoleucine | [CAS]
13139-16-7 | [Synonyms]
BOC-ILE-OH
BOC-ISOLEUCINE
BOC-L-ILE-OH
BOC-L-ISOLEUCINE
BOC-L-ISOLEUCINE-OH
N-ALPHA-T-BOC-L-ISOLEUCINE
N-ALPHA-T-BUTOXYCARBONYL-L-ISOLEUCINE
N-T-BOC-L-ISOLEUCINE
N-(TERT-BUTOXYCARBONYL)-L-ISOLEUCINE
n-[(1,1-dimethylethoxy)carbonyl]-l-isoleucin
N-Boc-L-isoleucine
N-T-BOC-L-ISOLEUCINE CRYSTALLINE
N-(TERT-BUTOXYCARBONYL)-L-ISOLEUCINE, 98 %
Boc-Ile-OH.5H2O
BOC-L-Isoleucine, 99+%
Boc-lle-OH.1/2H2O
boc-ile-oh,0.5h20
Boc-L-lle-OH
N-ALPHA-T-BUTYLOXYCARBONYL-L-ISOLEUCINE SEMIHYDRATE
Boc-L-isoleucine· 1/2H2O | [EINECS(EC#)]
236-074-8 | [Molecular Formula]
C11H21NO4 | [MDL Number]
MFCD00038324 | [Molecular Weight]
231.29 | [MOL File]
13139-16-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white fine crystalline powder | [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. ]
−20°C
| [solubility ]
Acetic Acid, DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.03±0.22(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]20/D +2.7°, c = 2 in acetic acid | [Water Solubility ]
Soluble in methanol. Insoluble in water. | [BRN ]
1711700 | [Major Application]
peptide synthesis | [InChI]
1S/C11H21NO4/c1-6-7(2)8(9(13)14)12-10(15)16-11(3,4)5/h7-8H,6H2,1-5H3,(H,12,15)(H,13,14)/t7-,8-/m0/s1 | [InChIKey]
QJCNLJWUIOIMMF-YUMQZZPRSA-N | [SMILES]
CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(O)=O | [CAS DataBase Reference]
13139-16-7(CAS DataBase Reference) | [EPA Substance Registry System]
13139-16-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29241990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 |
|
|