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4378-19-2

4378-19-2

Identification

Synonyms:2-amino-2,3-dimethyl-butanoic acid;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 12 Articles be found

Memory of chirality of tertiary aromatic amides: A simple and efficient method for the enantioselective synthesis of quaternary α-amino acids

Branca, Mathieu,Pena, Sebastien,Guillot, Regis,Gori, Didier,Alezra, Valerie,Kouklovsky, Cyrille

scheme or table, p. 10711 - 10718 (2009/12/04)

A new methodology for the asymmetric synthesis of quaternary R-substituted amino acids using memory of chirality has been developed. The strategy utilizes the dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during an enolization step. Starting from five different L-amino acids, the corresponding oxazolidin-5-ones containing a tertiary aromatic amide group have been synthesized in one step and then alkylated with various electrophiles, with good yields and enantioselectivities (up to 96% and up to >99% after recrystallization). One-step deprotection affords enantioenriched or enantiopure quaternary α-amino acids. We describe here the optimization process, the results obtained in each series and a plausible explanation, based on NMR studies, DFT calculations and crystallographic structures. The methodology presented herein constitutes an efficient synthesis of enantiopure quaternary R-amino acids (three steps only) starting from tertiary L-amino acids, without any external source of chirality.

Tertiary aromatic amide for memory of chirality: Access to enantioenriched α-substituted valine

Branca, Mathieu,Gori, Didier,Guillot, Regis,Alezra, Valerie,Kouklovsky, Cyrille

, p. 5864 - 5865 (2008/09/20)

A new methodology for the asymmetric synthesis of quaternary α-substituted amino acids using memory of chirality has been developed. This strategy employs dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during the enolization step. Starting from l-valine, an oxazolidin-5-one containing a tertiary aromatic amide was synthesized in one step and then alkylated with various electrophiles with good yield and enantioselectivity (up to 96%). Quaternary products can be obtained enantiomerically pure by recrystallization. One-step deprotection affords enantioenriched (S)-α-methyl valine (ee = 94%) or enantiopure (S)-α-isopropyl aspartic acid (ee >99%) in only three steps starting from L-valine. Copyright

L-phenylalanine cyclohexylamide: A simple and convenient auxiliary for the synthesis of optically pure α,α-disubstituted (R)- and (S)-amino acids

Obrecht,Bohdal,Broger,Bur,Lehmann,Ruffieux,Schonholzer,Spiegler,Muller

, p. 563 - 580 (2007/10/02)

This work describes L-phenylalanine cyclohexylamide (5c) as a simple, cheap, and powerful chiral auxiliary for the synthesis of a series of optically pure α,α-disubstituted (R)- and (S)-amino acids of type 1, such as (R)- and (S)-2-methyl-phenylalanine (1a), (R)- and (S)-2-methyl-2-phenylglycine (1b), and (R)- and (S)-2-methylvaline (1c). These amino acids were efficiently transformed into the suitably protected and activated amino-acid building blocks (R)- and (S)-12b and (R)- and (S)-12c which are ready for incorporation into peptides by solution or solid-phase techniques. Based on the crystal structures of 6b, 6c, and 7a belonging to the diastereoisomeric peptides series 6 and 7, the absolute configurations of each member of the series were determined. β-Turn geometries of type II' and I were observed for 6b and 7a, respectively, whereas 6c crystallized in an extended conformation. The impacts of side-chain variation on conformation and crystal packing of these triamides are discussed.

Process route upstream and downstream products

Process route

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one
1007599-18-9

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one

Conditions
Conditions Yield
With hydrogen bromide; In 1,4-dioxane; for 3h; Heating;
100%
(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one
1025364-74-2

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one

Conditions
Conditions Yield
(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one; With hydrogen bromide; In water; Reflux; Inert atmosphere;
With Dowex-H+; Inert atmosphere;
100%
(S)-methyl 2-benzamido-2,3-dimethylbutanoate

(S)-methyl 2-benzamido-2,3-dimethylbutanoate

Conditions
Conditions Yield
With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 12h;
87.4%
(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid
137584-40-8

(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid

Conditions
Conditions Yield
With 10% Pd on charcoal; cyclohexene; In ethanol; for 1h; Reflux;
83%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

(+)-(R)-2-amino-2,3-dimethylbutanamide
90376-98-0

(+)-(R)-2-amino-2,3-dimethylbutanamide

Conditions
Conditions Yield
In water; at 37 ℃; Ochrobactrum anthropi NCIMB 40321;
74%
86%
With water; at 37 ℃; for 72h; aminopeptidase from Mycobacterium neoaurum ATCC 25795;
(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on
97443-93-1

(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
2: tetrahydrofuran; hexane / 2 h / -78 - 0 °C
3: 1.) 6 N HCl, 2.) Dowex 50 WX / 1.) water, 175 deg C to 185 deg C, 4 h; 2.) water
With hydrogenchloride; Dowex 50 WX; lithium diisopropyl amide; In tetrahydrofuran; hexane;
Lithium; (R)-1-benzoyl-2-tert-butyl-5-isopropyl-3-methyl-2,3-dihydro-1H-imidazol-4-olate

Lithium; (R)-1-benzoyl-2-tert-butyl-5-isopropyl-3-methyl-2,3-dihydro-1H-imidazol-4-olate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrahydrofuran; hexane / 2 h / -78 - 0 °C
2: 1.) 6 N HCl, 2.) Dowex 50 WX / 1.) water, 175 deg C to 185 deg C, 4 h; 2.) water
With hydrogenchloride; Dowex 50 WX; In tetrahydrofuran; hexane;
DL-N-Trifluoroacetyl-α-methylvalin
53940-86-6

DL-N-Trifluoroacetyl-α-methylvalin

Conditions
Conditions Yield
With sodium hydroxide; (enzymatic transformation);
(SS)-{Ni(O<sub>2</sub>CC(CH(CH<sub>3</sub>)2)(CH<sub>3</sub>)NCHC<sub>6</sub>H<sub>4</sub>NCOC<sub>4</sub>H<sub>7</sub>N(CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>))}*1.5H<sub>2</sub>O

(SS)-{Ni(O2CC(CH(CH3)2)(CH3)NCHC6H4NCOC4H7N(CH2C6H5))}*1.5H2O

Conditions
Conditions Yield
75%
(2S) methyl 2-methoxycarbonylamino-2,3-dimethylbutanoate

(2S) methyl 2-methoxycarbonylamino-2,3-dimethylbutanoate

Conditions
Conditions Yield
With hydrogenchloride; methyloxirane; Yield given. Multistep reaction; 1.) reflux, 12 h, 2.) EtOH, reflux, 30 min;

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