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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
2-(benzothiazole-2-sulfonylamino)-3-(4-<i>tert</i>-butoxy-phenyl)-propionic acid[ No CAS ]
[ 22838-58-0 ]
[ 53308-95-5 ]
15-(4-hydroxy-benzyl)-12-isopropyl-9-propyl-5,6,7,9,10,12,13,15,16,17,18,19-dodecahydro-7,10,13,16-tetraaza-benzocycloheptadecene-8,11,14-trione[ No CAS ]
2-(benzothiazole-2-sulfonylamino)-3-(4-<i>tert</i>-butoxy-phenyl)-propionic acid[ No CAS ]
[ 22838-58-0 ]
[ 53308-95-5 ]
15-(4-hydroxy-benzyl)-12-isopropyl-9-propyl-6,7,9,10,12,13,15,16,17,18,19,20-dodecahydro-5<i>H</i>-7,10,13,16-tetraaza-benzocyclooctadecene-8,11,14-trione[ No CAS ]
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