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Quality Control of Boc-Val-OH Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Boc-Val-OH

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

Safety of Boc-Val-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Boc-Val-OH

* 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.

Downstream synthetic route of [ 13734-41-3 ]

[ 13734-41-3 ] Synthesis Path-Downstream 1~30

1
[ 13734-41-3 ]
[ 2886-33-1 ]
[ 70853-19-9 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 2288 - 2290.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 4396 - 4407.

2
[ 169556-48-3 ]
[ 13734-41-3 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 1265 - 1268.

3
[ 13734-41-3 ]
Boc-DTrp, Boc-Bta, Boc-DCys(4-methylbenzyloxycarbonyl), Boc-Nal [ No CAS ]
[ 5699-54-7 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 7764 - 7769.

4
[ 13734-41-3 ]
[ 69558-55-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 2507 - 2511.
[2]Journal of Materials Chemistry B,2016,vol. 4,p. 1384 - 1397.

5
[ 13734-41-3 ]
[ 16741-80-3 ]
[ 57281-71-7 ]

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%).

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7056 - 7059.
[2]Tetrahedron,2015,vol. 71,p. 1117 - 1123.

6
[ 15761-39-4 ]
[ 13734-41-3 ]
[ 13139-15-6 ]
[ 15761-38-3 ]
C₁₆H₂₈N₃O₅PolS [ No CAS ]
[ 7536-55-2 ]
[ 13726-85-7 ]
[ 13574-13-5 ]
[ 13836-37-8 ]
[ 23680-31-1 ]
[ 47355-10-2 ]
[ 83468-83-1 ]
Fmoc-Asp-Cys(Acm)-His-Leu-Gln-Ala-Val-Val-Leu-His-Leu-Ala-Arg-Arg-Ser-Val-Cys(Acm)-Val-His-Pro-Gln-Asn-Arg-Ser-Leu-Ala-Arg-Trp-Leu-Glu-Arg-Gln-Gly-S-CH₂CH₂CO-Leu-NH₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1808 - 1813.

7
boc-Gly-Merrifield resin [ No CAS ]
[ 15761-39-4 ]
[ 13734-41-3 ]
[ 13836-37-8 ]
[ 54613-99-9 ]
[ 81-88-9 ]
[ 108466-89-3 ]
[ 1229593-79-6 ]

References: [1]European Journal of Organic Chemistry,2010,p. 2441 - 2444.

8
[ 13734-41-3 ]
[ 84605-18-5 ]
[ 1255151-80-4 ]

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.

References: [1]Patent: US2010/292197,2010,A1 .Location in patent: Page/Page column 14-15.

9
[ 13734-41-3 ]
[ 84605-18-5 ]
[ 1255151-83-7 ]

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.

References: [1]Patent: US2010/292197,2010,A1 .Location in patent: Page/Page column 16.

10
[ 13734-41-3 ]
[ 2886-33-1 ]
[ 70853-21-3 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 4396 - 4407.

11
[ 4530-20-5 ]
[ 13734-41-3 ]
[ 13139-16-7 ]
[ 13139-15-6 ]
[ 15761-38-3 ]
[ 13734-34-4 ]
[ 13836-37-8 ]
[ 73821-97-3 ]
[ 54613-99-9 ]
[ 47689-67-8 ]
[ 47355-10-2 ]
HAEGTFTSDVSSYLEGQAAKEFIAWLVKGRG-OH [ No CAS ]