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Boc-Val-OH is a valine derivative, used for peptide synthesis and as a biochemical reagent.
Synonyms: Boc-L-Valine
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 13734-41-3 |
Formula : | C10H19NO4 |
M.W : | 217.26 |
SMILES Code : | CC(C)[C@H](NC(OC(C)(C)C)=O)C(O)=O |
Synonyms : |
Boc-L-Valine
|
MDL No. : | MFCD00065605 |
InChI Key : | SZXBQTSZISFIAO-ZETCQYMHSA-N |
Pubchem ID : | 83693 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; | General procedure: EDC hydrochloride (1.1 equiv) and HOBt (1.2 equiv) were added to solutions of N-BocValOH (1. 0equiv), amino acid methyl ester hydrochlorides (Xaa=ValOMe, PheOMe, MetOMe, SerOMe, TyrOMe, TrpOMe, Csy(S-Bn)OMe, 1.0 equiv), and i-Pr2NEt (1.1 equiv) in DMF at 0C. The mixtures were stirred for 2 h at 0C and overnight at room temperature, and concentrated in vacuo. The residues were dissolved in CH2Cl2, and washed with 4% NaHCO3, 1M HCl, and water. The organic layer was dried over Na2SO4 and concentrated in vacuo, giving residues that were subjected to silica gel column chromatography using hexane/AcOEt or CH2Cl2/AcOEt as eluents to give the desired protected dipeptides N-BocValXaaOMe (75-90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Preparation of 3: Boc-(L)-Valine-OH (18 g, 81.63 mmols) (Bachem, Torrance, Calif.) was dissolved in 150 ml of dichloromethane (DCM). To this was added 15 g (81.63 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 12.8 ml (81.63 mmols) of 1,3 diisopropylcarbodiimide (DIC). After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 10 g (20.41 mmols) of (2) followed by 10 g (81.63 mmol) of dimethylaminopyridine (DMAP) and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a sepratory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. The residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 7.0 g (50%) of the target product 3 together with 6.0 g, (33%) of the bis product.1HNMR for 3: (CDCl3) delta ppm: 0.38 (1H, bs), 0.52 (1H, bs), 0.90-1.38 (m, 30H), 1.39-1.45 (s,m 12H), 1.59-1.63 (m, 5H), 1.76-1.82 (m, 2H), 1.96-2.01 (m, 4H), 2.16-2.20 (m, 1H), 2.30-2.35 (d, 1H), 2.49-2.54 (q, 1H), 3.45-3.57 (t, 1H), 3.71-3.76 (t, 1H), 4.19-4.21 (m, 1H), 4.53-4.61 (m, 1H), 4.69-4.71 (q, 1H), 5.0-5.2 (d, 1H. MS (M+H) 690. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Preparation of 6: Boc-(L) Valine-OH (10 g, 46.08 mmols) was dissolved in 80 ml of N-methylpyrrolidone (NMP). To this was added 8.5 g (46.08 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 7.2 ml (46.08 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 3.2 g (6.60 mmols) of 2 followed by 5.5 g (45 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a sepratory funnel and washed successively with H2O (6×), 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. The residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 4.8 g (83%) of the target product 6.1HNMR for 6: (CDCl3) delta ppm: 0.38 (1H, bs), 0.60 (1H, bs), 0.80-1.0 (m, 24H), 1.15 (s,s 6H), 1.20 (s,s 6H), 1.31 (s, 6H), 1.35 (s,s 4H)1.41 (s,s 18H), 1.56-1.60 (m, 4H), 1.79-1.83 (m, 3H), 3.71-3.76 (t, 1H), 4. 08-4.21 (m, 2H), 4.58-4.60 (m, 1H), 4.61-4.70 (q, 1H), 4.72-4.80 (m, 1H), 4.82-4.84 (d, 1H), 4.9-5.0 (d, 1H). MS (M+H) 889. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.5% | To a stirred solution of N-(tert-butoxycarbonyl)valine (Step A, 7.05 g, 32.4 mmol) intetrahydrofuran (65 mL) was added 1,1-carbonyldimidazole (5.25 g, 32.4 mmol), and the reactionmixture was stirred at ambient temperature for 10 minutes. Then a solution of sodium borohydride(1.96 g, 51.8 mmol) in water (32 mL) was added. The resulting solution was stirred at ambienttemperature for 12 hours. Then the mixture was diluted with ethyl acetate (200 mL), and the organic20 layer was separated, washed with 1 N hydrochloric acid (1 00 mL) and brine ( 60 mL ), dried over25Na2S04, passed through a short pad of Si02, and concentrated to afford 5. 7 g, 86.5% of the titledcompound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 0.76-0.90 (m, 6H), 1.38 (s, 9H),1.73-1.80(m, 1H), 3.17-3.40 (m, 3H), 4.42 (t, J=5.5Hz, 1H), 6.36(m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.2% | The titled peptide was synthesized on a model 430A peptide synthesizer (Applied Rio systems, Foster City, Calif., U.S.A.) which was modified to do accelerated Hoc-chemistry solid phase peptide synthesis (Schnolzer, M. et al., mt. J Peptide Protein Res., (1992), 40:180). 4-Methylbenzhydry- lamine (MHHA) resin (Peninsula, Helmont, Calif., U.S.A.), with a substitution of0.91 mmol/g was used. Hoc amino acids (Midwest Hio-Tech, Fishers, Ind., U.S.A.; Novabiochem., San Diego, Calif., U.S.A.) were used with the following side chain protection: Hoc-Ala-OH, Hoc-Arg(Tos)-OH, Hoc-His (DNP)-OH, Hoc-Val-OH, Hoc-Ecu-OH, Hoc-Gly-OH, HocGln-OH, Hoc-Eys(2C1Z)?--OH, Hoc-Ser(Hzl)-OH, Hoc-PheOH, Hoc-Glu(OcHex)-OH and Hoc-Pro-OH. Fmoc-Glu (OtHu)-OH (Novabiochem, San Diego, Calif., U.S.A.) was used for the residue at the 3rd position in the sequence. The synthesis was carried out on a 0.25 mmol scale. The Hoc groups were removed by two treatments with 100percent TFA each lasting one minute. Hoc amino acids (2.5 mmol) were preactivated with HH11J (2.0 mmol) and DIEA (1.0 mE) in 4 mE of DMF and were coupled without prior neutralization of the peptide-resin TFA salt. Coupling times were 5 minutes. At the end of the assembly of the first 25 residues on theAHI 430A® peptide synthesizer and before the coupling of Fmoc-Glu (OtHu)-OH, the protected peptide-resin was transferred into a reaction vessel on a shaker for manual synthesis. After removing the Hoc protecting group with two, one-minute treatments with 100percent TFA and a washing with DMF, the resin was mixed with Fmoc-Glu(OtHu)-OH (2.5 mmol) which was preactivated with HHTU (2.0 mmol), HOHt (2.0 mmol) and DIEA (1.0 mE) in 4 mE of DMF. The mixture was shaken for 2 hours. This coupling step was repeated. After washing with DMF, the resin was treated with a TFA solution containing 5percent water and 5percent TIS for 2 hours to remove the tHu protecting group in the side chain of the Glu residue. The resin was neutralized with 10percent DIEA in DMF and washed with DMF and DCM. The resin was then treated twice with hexylamine (2.0 mmol), DIC (2.0 mmol), HOHt (2.0 mmol) in 5 ml of DCM for two hours per treatment. The resin was washed with DMF and treated with 25percent piperidine in DMF for 30 minutes to remove the Fmoc protecting group. Afier washing with DMF and DCM, the resin was transferred into the reaction vessel on the AHI 430A peptide synthesizer for the assembly of the rest two residues. At the end of the assembly of the whole peptide chain, the resin was treated with a solution of 20percent mercaptoethanol/10percent DIEA in DMF for 2x30 mm to remove the DNP group on the His side chain. The N-terminal Hoc group was then removed by two treatments of 100percent TFA for 2 minutes. The peptide-resin was washed with DMF and DCM and dried under reduced pressure. The final cleavage was done by stirring the peptide-resin in 10 mE of HF containing 1 mE of anisole and dithiothreitol (50 mg) at 0° C. for 75 minutes. HF was removed by a flow of nitrogen. The residue was washed with ether (6x 10 mE) and extracted with 4N HOAc (6x10 mE). This crude product was purified on a reverse-phase preparative HPEC using a colunm (4x43 cm) of C18 DYNAMAX-100A°® (Varian, Walnut Creek, Calif., U.S.A.). The column was eluted with a linear gradient from 75percentAand25percent B to 55percentAand45percent B at flow rate of 10 mE/mm in an hour where A was 0.1percent TFA in water and B was 0.1percent TFA in acetonitrile. Fractions were collected and checked on an analytical HPEC. Those containing pure product were combined and lyophilized to dryness. 31.8 mg of a white solid was obtained. Purity was 89percent based on analytical HPEC analysis. Electro-spray ionization mass spectrometry (ESI MS) analysis gave the molecular weight at 3368.4 (in agreement with the calculated molecular weight of 3368.9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.4% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;Inert atmosphere; | Irinotecan (13.0 g, 22.2 mmol) was dissolved in dichloromethane (500 mL) and N-tert-butyloxycarbonylvaline(9.63 g, 44.4 mmol), DMAP (5.42 g, 44.4 mmol). Under a nitrogen atmosphere, EDC (12.80 g, 66.7 mmol) in dichloromethane (280 mL) and the system was allowed to react overnight at room temperature. The reaction was complete by TLC and the reaction was washed with distilled water (500 mL) and saturated sodium chloride solution (500 mL) Drying over anhydrous sodium sulfate. Concentrated to dryness, the residue was purified by silica gel column, isopropyl ether precipitation, Drying under vacuum at room temperature to give a pale yellow solid 12.63g, yield 72.4percent |