Tert-butyl N-methyl-L-valinate
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Tert-butyl N-methyl-L-valinate

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Category
L-Amino Acids
Catalog number
BAT-009007
CAS number
5616-87-5
Molecular Formula
C10H21NO2
Molecular Weight
178.28
IUPAC Name
tert-butyl (2S)-3-methyl-2-(methylamino)butanoate
Synonyms
Me-Val-OtBu; Me Val OtBu; Tert-butyl (2S)-3-methyl-2-(methylamino)butanoate
InChI
InChI=1S/C10H21NO2/c1-7(2)8(11-6)9(12)13-10(3,4)5/h7-8,11H,1-6H3/t8-/m0/s1
InChI Key
GQQBJNNCJGGHJG-QMMMGPOBSA-N
Canonical SMILES
CC(C)C(C(=O)OC(C)(C)C)NC
1. N-tert-Butyl-3-mesitylpropanamide
Abel M Maharramov, Ali N Khalilov, Atash V Gurbanov, Iván Brito Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):o1307. doi: 10.1107/S1600536811015856. Epub 2011 May 7.
In the title compound, C(16)H(25)NO, the N-tert-butyl-propanamide fragment is essentially planar, with the exception of two C atoms of the tert-butyl group (r.m.s. deviation = 0.005 Å), forming a dihedral angle of 84.09 (10)° with the plane of the mesityl fragment (r.m.s. deviation = 0.002 Å). The crystal packing is stabilized by an inter-molecular N-H⋯O hydrogen bond, which links the mol-ecules into chains with graph-set notation C(4) running parallel to the c axis.
2. (R)-N-{2-tert-Butyl-2-[(R)-tert-butyl-sulfonamido]ethylidene}-tert-butane-sulfonamide
Yu Hu, Xiao-Xia Sun, Cong-Bin Fan Acta Crystallogr Sect E Struct Rep Online. 2008 Sep 13;64(Pt 10):o1913. doi: 10.1107/S1600536808028225.
The title compound, C(14)H(30)N(2)O(2)S(2), is the product of the monoaddition reaction of tert-butyl magnesium chloride with bis-[(R)-N-tert-butanesulfinyl]ethanediimine. There are two almost identical mol-ecules in the asymmetric unit, the mol-ecular conformation of which is stabilized by an intra-molecular N-H⋯N hydrogen bond.
3. Synthesis of O- tert-Butyl- N,N-disubstituted Hydroxylamines by N-O Bond Formation
Jarvis Hill, David Crich Org Lett. 2021 Aug 20;23(16):6396-6400. doi: 10.1021/acs.orglett.1c02215. Epub 2021 Jul 30.
The reaction of magnesium amides with tert-butyl 2,6-dimethyl perbenzoate in tetrahydrofuran at 0 °C provides a method for the synthesis O-tert-butyl-N,N-disubstituted hydroxylamines by direct N-O bond formation with a broad functional group tolerance. Less sterically hindered magnesium amides require ortho,ortho-disubstitution on the perester electrophile component, whereas sterically encumbered magnesium amides perform comparably with either tert-butyl perbenzoate or tert-butyl 2,6-dimethyl perbenzoate. A reaction mechanism is presented to account for the observed reactivity.
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