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Quality Control of Boc-D-Val-OH Purity: 99% 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-D-Val-OH

CAS No. :	22838-58-0
Formula :	C₁₀H₁₉NO₄
M.W :	217.26
SMILES Code :	CC(C)[C@@H](NC(OC(C)(C)C)=O)C(O)=O
Synonyms :	tert-Butoxycarbonyl-D-valine; N-tert-Butyloxycarbonyl-D-valine; NSC 334316
MDL No. :	MFCD00038282
InChI Key :	SZXBQTSZISFIAO-SSDOTTSWSA-N
Pubchem ID :	637605

Safety of Boc-D-Val-OH

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

Application In Synthesis of Boc-D-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 [ 22838-58-0 ]

[ 22838-58-0 ] Synthesis Path-Downstream 1~24

1
[ 22838-58-0 ]
[ 74-88-4 ]
[ 13850-91-4 ]

Yield	Reaction Conditions	Operation in experiment
84%		To N-Boc D-valine (5 g, 11.5 mmol) at 0 C in THF (69 mL, 0.35 M) is added MeI (11.45 mL, 8 eq). NaH (60% dispersion in mineral oil, 2.76 g, 3eq) is then added carefully to the stirring solution portionwise. The mixturewas allowed to stir vigorously overnight at room temperature before beingdiluted with Et2O (70 mL) and quenched slowly with H2O (50 mL) at 0 C.The layers were separated and the aqueous layer extracted twice with Et2O(2 x 30 mL). The aqueous layer was brought to ~pH 2 with the dropwise addition of conc. HCl(checking the pH by spotting the aqueous layer onto pH paper) and extracted with EtOAc (4 x100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, andconcentrated in vacuo. The resulting oil (4.46 g, 84% yield) was sufficiently pure for the nextstep. If desired, an analytical sample could be obtained as a white fluffy solid after flash columnchromatography (silica gel, 3%-5% MeOH/DCM). The use of only 3 eq of MeI in a similarprocedure resulted in the appearance of starting material at the end of the reaction, presumablydue to competitive precipitation of the disodium salt.3

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2090 - 2111.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Tetrahedron Letters,2012,vol. 53,p. 4077 - 4079.
[4]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1140 - 1150.
[5]Tetrahedron,1995,vol. 51,p. 10653 - 10662.
[6]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[7]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7027 - 7030.
[8]Current Medicinal Chemistry,2013,vol. 20,p. 1183 - 1194.

2
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2-(benzothiazole-2-sulfonylamino)-3-(4-tert-butoxy-phenyl)-propionic acid [ No CAS ]
[ 22838-58-0 ]
[ 53308-95-5 ]
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