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595-40-4

595-40-4 Structure

595-40-4 Structure
IdentificationMore
[Name]

L-Isovaline
[CAS]

595-40-4
[Synonyms]

D(-)-ISOVALINE
(R)-(-)-2-AMINO-2-METHYLBUTANOIC ACID
(R)-2-AMINO-2-METHYLBUTYRIC ACID
(S)-2-Amino-2-Methylbutanoic Acid
(S)-(+)-2-Amino-2-methylbutanoicacidmonohydrate(e.e.)
(S)-(+)-2-AMINO-2-METHYLBUTANOIC ACID 1-HYDRATE (E.E.)
(S)-(+)-2-Amino-2-methylbutanoic acid monohydrate
L-Isovaline
L-ISO-VALINE((S)-2-AMINO-2-METHYLBUTANOIC ACID)
(S)-alpha-Ethylalanine (>98%, >99%ee)
H-alpha-Et-D-Ala-OH
2,3-Dimethylalanine
[Molecular Formula]

C5H11NO2
[MDL Number]

MFCD00800497
[Molecular Weight]

117.15
[MOL File]

595-40-4.mol
Chemical PropertiesBack Directory
[Melting point ]

289.39°C (estimate)
[alpha ]

D25 +11.13° (c = 5 in H2O)
[Boiling point ]

213.6±23.0 °C(Predicted)
[density ]

1.2000 (estimate)
[refractive index ]

1.4650 (estimate)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[form ]

Fine Crystalline Powder
[pka]

2.38±0.10(Predicted)
[color ]

White
[Optical Rotation]

Consistent with structure
[InChI]

InChI=1S/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m1/s1
[InChIKey]

GCHPUFAZSONQIV-RXMQYKEDSA-N
[SMILES]

C(O)(=O)[C@](CC)(C)N
[CAS DataBase Reference]

595-40-4(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[TSCA ]

No
Hazard InformationBack Directory
[Uses]

a-Me-Gly(Ethyl)-OH is used in preparation of peptide compound comprising highly sterically hindered amino acid via reaction of electron-withdrawing group-protected N-unsubstituted-α,α-disubstituted amino acid with peptide followed by N-alkylation.
[Synthesis]

ETHYL (S)-2-AMINO-2-METHYLBUTYRATE

13893-46-4

L-Isovaline

595-40-4

1.4) Compound F1 (13.8 g, 95.0 mmol) and sodium hydroxide (7.6 g, 190.08 mmol) were added sequentially to a mixture of ethanol (200 mL) and water (1:1 by volume) and heated to reflux for 4 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with 2 M hydrochloric acid solution, followed by evaporation of the solvent. The residue was dissolved in a small amount of water and purified by strongly acidic cation exchange resin 732. The final product G1 (10 g, 90% yield) was obtained as a white solid.

[Purification Methods]

Crystallise it from aqueous Me2CO, or better by dissolving in H2O and adding excess Me2CO. [Baker et al. J Am Chem Soc 74 4701 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2573-2577 1961.]
[References]

[1] Patent: CN108440320, 2018, A. Location in patent: Paragraph 0033; 0035; 0043
Spectrum DetailBack Directory
[Spectrum Detail]

L-Isovaline(595-40-4)1HNMR
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