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O-tert-Butyl-L-serine methyl ester hydrochloride

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Category

L-Amino Acids

Catalog number

BAT-004175

CAS number

17114-97-5

Molecular Formula

C8H17NO3.HCl

Molecular Weight

211.69

O-tert-Butyl-L-serine methyl ester hydrochloride

Specification
Reference Reading

IUPAC Name

methyl (2S)-2-amino-3-[(2-methylpropan-2-yl)oxy]propanoate;hydrochloride

Synonyms

L-Serine, O-(1,1-dimethylethyl)-, methyl ester, hydrochloride (1:1); Alanine, 3-tert-butoxy-, methyl ester, hydrochloride; Alanine, 3-tert-butoxy-, methyl ester, hydrochloride, L-; (S)-2-Amino-3-tert-butoxypropionic acid methyl ester hydrochloride; Methyl (2S)-2-amino-3-tert-butoxypropanoate hydrochloride; Methyl (S)-2-amino-3-tert-butoxypropanoate hydrochloride; O-tert-Butyl-(S)-serine methyl ester hydrochloride; O-tert-Butylserine methyl ester hydrochloride

Related CAS

52799-79-8 (Deleted CAS) 17083-26-0 (free base)

Appearance

White powder

Purity

≥95%

Melting Point

171-172°C

Storage

Store at 2-8°C

InChI

InChI=1S/C8H17NO3.ClH/c1-8(2,3)12-5-6(9)7(10)11-4;/h6H,5,9H2,1-4H3;1H/t6-;/m0./s1

InChI Key

PCIABNBULSRKSU-RGMNGODLSA-N

Canonical SMILES

CC(C)(C)OCC(C(=O)OC)N.Cl

1. An efficient enantioselective synthesis of ( S)-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination

Qiong Xiao, Yi-Fan Tang, Ping Xie J Asian Nat Prod Res. 2020 Jan;22(1):61-68. doi: 10.1080/10286020.2019.1634058. Epub 2019 Jul 16.

We present the synthesis of enantiomerically pure (S)-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di-p-chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine derivative catalyst. The application of the organocatalyst of D-3-(1-Naphthyl)-alanine is the key step in the synthesis and ensures the product is obtained with high levels of stereocontrol.

2. l-Serine methyl ester hydro-chloride

Arie Schouten, Martin Lutz Acta Crystallogr Sect E Struct Rep Online. 2009 Nov 7;65(Pt 12):o3026. doi: 10.1107/S1600536809046480.

In the enanti-opure crystal of the title compound, C(4)H(10)NO(3) (+)·Cl(-), inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds link the mol-ecules into layers parallel to (001).