55686-06-1

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55686-06-1

Product Name:5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-
CAS Number: 55686-06-1
EINECS:
Molecular Weight:265.312
Molecular Formula: C17H15NO2
HS Code:
Mol File:55686-06-1.mol

Synonyms:

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Chemical Properties

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 6 Articles be found

BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids

Lee, Yeon-Ju,Seo, Jeyoung,Kim, Dong-Guk,Park, Hyeung-Geun,Jeong, Byeong-Seon

, p. 701 - 704 (2013/05/09)

Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free α,α-dialkyl-α-amino acids, were obtained in high yields (up to 99%

Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones

Trost, Barry M.,Czabaniuk, Lara C.

, p. 5778 - 5781 (2012/05/07)

Palladium-catalyzed asymmetric benzylation has been demonstrated with azlactones as prochiral nucleophiles in the presence of chiral bisphosphine ligands. Benzylic electrophiles are utilized under two sets of reaction conditions to construct a new tetrasubstituted stereocenter. Electron density of the phenyl ring dictates the reaction conditions, including the leaving group. The reported methodology represents a novel asymmetric carbon-carbon bond formation in an amino acid precursor.

A reinvestigation of the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones ('azlactones'): A general entry into highly functionalized α,α-disubstituted α-amino acids

Obrecht,Bohdal,Ruffieux,Muller

, p. 1423 - 1429 (2007/10/02)

Novel, more reliable and general reaction conditions for the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones (= 4-monosubstituted 2-phenyl-azlactones) rac-2 to 4,4-disubstituted 2-phenyloxazol-5(4H)-ones rac-1 were found. Thus, a whole range of highly functionalized rac-1 were prepared in medium-to-good overall yields (40-90%). Azlactones rac-1 are ideal precursors for the synthesis of optically pure α,α-disubstituted (R)- and (S)-α-amino acids.

Process route upstream and downstream products

Process route

: 2566-22-5,2901-76-0,37002-52-1
DL-N-benzoylphenylalanine

: 55686-06-1
rac-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 30 min, 0 deg C, 2.) 1 h, room temperature 2: 55 percent NaH / dimethylformamide / 1.) 30 min, 10 - 15 deg C, 2.) 2 h, room temperature With sodium hydride; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

: 5874-61-3,21453-79-2,51127-19-6,75658-67-2
4-benzyl-2-phenyl-2-oxazolin-5-one

: 74-88-4
methyl iodide

: 55686-06-1
rac-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Reagent/catalyst; Solvent; Temperature; Time;	90%
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
With sodium hydride; In N,N-dimethyl-formamide; Yield given; 1.) 30 min, 10 - 15 deg C, 2.) 2 h, room temperature;
With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; for 288h; Ambient temperature;

: N²-<(R)-N²-benzoyl-2-methylphenylalanyl>-L-phenylalanine dimethylamide

: 55686-06-1,96574-50-4,144646-17-3,96574-49-1
(R)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With hydrogenchloride; In toluene; at 80 ℃; for 0.5h;	89%

: N²-<(S)-N²-benzoyl-2-methylphenylalanyl>-L-phenylalanine dimethylamide

: 55686-06-1,96574-49-1,144646-17-3,96574-50-4
(S)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With hydrogenchloride; In toluene; at 80 ℃; for 0.5h;	85%

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 4218-62-6
benzyl diphenyl phosphate

: 55686-06-1,96574-50-4,144646-17-3,96574-49-1
(R)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; tert-butyl alcohol; In 1,4-dioxane; at 50 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;	83%

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 1369423-47-1
diphenyl 4-fluorobenzyl phosphate

: 55686-06-1,96574-50-4,144646-17-3,96574-49-1
(R)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; tert-butyl alcohol; In 1,4-dioxane; at 50 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;	74%

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 884-90-2
benzyl diethyl phosphate

: 55686-06-1,96574-50-4,144646-17-3,96574-49-1
(R)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; tert-butyl alcohol; In dichloromethane; at 25 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;	38%

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 884-90-2
benzyl diethyl phosphate

: 55686-06-1,96574-49-1,144646-17-3,96574-50-4
(S)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; In dichloromethane; at 25 ℃; for 20h; Reagent/catalyst; Solvent; enantioselective reaction; Inert atmosphere;	36%

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 100-39-0
benzyl bromide

: 55686-06-1
rac-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 75 - 80 ℃; for 8.5h;
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; at 20 ℃; for 0.0166667h;

: 51127-13-0,71963-72-9,87480-74-8,13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 4218-62-6
benzyl diphenyl phosphate

: 55686-06-1,96574-49-1,144646-17-3,96574-50-4
(S)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

: 55686-06-1,96574-50-4,144646-17-3,96574-49-1
(R)-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; tert-butyl alcohol; In 1,4-dioxane; at 50 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

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Cas Database

55686-06-1

55686-06-1

Identification

Product Name:5(4H)-Oxazolone, 4-methyl-2-phenyl-4-(phenylmethyl)-

CAS Number: 55686-06-1

EINECS:

Molecular Weight:265.312

Molecular Formula: C17H15NO2

HS Code:

Mol File:55686-06-1.mol

Synonyms:

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Chemical Properties

Safety information and MSDS view more

Signal Word:no data available

Hazard Statement:no data available

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.

Supplier and reference price view more

Relevant articles and documentsAll total 6 Articles be found

BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids

Lee, Yeon-Ju,Seo, Jeyoung,Kim, Dong-Guk,Park, Hyeung-Geun,Jeong, Byeong-Seon

, p. 701 - 704 (2013/05/09)

Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones

Trost, Barry M.,Czabaniuk, Lara C.

, p. 5778 - 5781 (2012/05/07)

A reinvestigation of the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones ('azlactones'): A general entry into highly functionalized α,α-disubstituted α-amino acids

Obrecht,Bohdal,Ruffieux,Muller

, p. 1423 - 1429 (2007/10/02)

Process route upstream and downstream products

Process route

55686-06-1 Upstream products

55686-06-1 Downstream products

Global suppliers and manufacturers

Remarks: The blank with*must be completed