(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone supplier

Name
(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
EINECS
CAS No. 77943-39-6
Article Data90
CAS DataBase
Density 1.132 g/cm³
Solubility
Melting Point 121-123 °C(lit.)
Formula C₁₀H₁₁NO₂
Boiling Point 395.8 °C at 760 mmHg
Molecular Weight 177.203
Flash Point 193.2 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25
Risk Codes N:;
Molecular Structure
Hazard Symbols N
Synonyms 2-Oxazolidinone,4-methyl-5-phenyl-, (4R-cis)-;(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone;(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone;(4R,5S)-4-Methyl-5-phenyloxazolidinone;
PSA 38.33000
LogP 2.18480

Synthetic route

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 779353-80-9
(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

A: 541511-47-1
(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

B: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In tetrahydrofuran; toluene at 0 - 20℃; Stage #2: (4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one In tetrahydrofuran; toluene at 0℃; for 1h;	A 100% B 272 mg

...Expand

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 70-07-5
mephenoxalone

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane	100%
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane	100%
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane	100%

: 201230-82-2
carbon monoxide

: 37577-28-9
(1S,2R)-(+)-norphedrine

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating;	99%
With sodium acetate; palladium diacetate In acetonitrile at 20℃; under 760 Torr; Electrolysis;	86%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 132969-62-1
(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4"-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 252342-49-7
(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

Conditions

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In tetrahydrofuran; hexane at 0 - 20℃; Metallation; Stage #2: (2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4"-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone In tetrahydrofuran; hexane at -20℃; for 2.5h; Substitution; Further stages.;	A 80% B 98%

...Expand

: 124-38-9
carbon dioxide

: 37577-28-9
(1S,2R)-(+)-norphedrine

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With triethylamine; acetyl chloride In acetonitrile at -40 - 25℃;	97%
Stage #1: carbon dioxide; (1S,2R)-(+)-norphedrine With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.75h; Stage #2: With tributylphosphine; di-tert-butyl-diazodicarboxylate In acetonitrile at 0℃; for 0.333333h; Mitsunobu reaction;	84%
With tetramethylphenylguanidine; chlorophosphoric acid diphenyl ester In acetonitrile at -40 - 20℃;	82%
Stage #1: carbon dioxide; (1S,2R)-(+)-norphedrine With N(Et)4(1+)*(2-pyrrolidone-anion) In acetonitrile at 20℃; for 1h; Carboxylation; Stage #2: With p-toluenesulfonyl chloride In acetonitrile at 20℃; Cyclization; Further stages.;	79%

: 179927-67-4
(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 179927-65-2
5-O-benzyl-2-deoxy-2-fluoro-L-γ-xylonic lactone

C: 179927-64-1
5-O-benzyl-2-deoxy-2-fluoro-D-γ-xylonic lactone

Conditions

Conditions	Yield
With osmium(VIII) oxide; trimethylamine-N-oxide In water; acetone; tert-butyl alcohol at 20℃; for 2h; Oxidation; cyclization;	A n/a B 94% C 86%

...Expand

: 102-09-0
bis(phenyl) carbonate

: 40626-29-7
Acutrim

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With potassium carbonate at 110℃; for 6h;	93%
Stage #1: bis(phenyl) carbonate; Acutrim With potassium carbonate at 100℃; for 6h; Stage #2: In methanol for 0.5h; Heating;

: 954106-23-1
C37H45NO6

A: 954106-40-2
C27H36O5

B: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 2h;	A 92% B 79%

: 128891-59-8
(4R,5S)-3-[(Z)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-dec-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 126617-76-3
(2R,4Z)-2(tert-Butyldiphenylsiloxy)-4-decen-1-ol

Conditions

Conditions	Yield
With lithium borohydride; water In tetrahydrofuran; diethyl ether Product distribution; Ambient temperature; other reducing reagents; var. N-acyloxazolidinones;	A n/a B 90%

: 109687-75-4
(4R,5S)-3-((R)-2-Benzyl-4-methyl-pent-3-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 109687-76-5
4-methyl-2(R)-(phenylmethyl)-3-penten-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 0℃; for 1.5h;	A 70% B 90%

: 80697-94-5
(2'S,4R,5S)-3-(2'-methyl-3'-phenylpropionyl)-4-methyl-5-phenyloxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 7384-80-7, 77943-96-5, 78964-61-1, 22436-06-2
(S)-2-methyl-3-phenylpropan-1-ol

Conditions

Conditions	Yield
With Cp*RuCl{(C6H5)2P-(CH2)2NH2-κ2-P,N}; potassium tert-butylate; hydrogen In isopropyl alcohol at 80℃; under 22502.3 Torr; for 20h; Autoclave; optical yield given as %ee;	A 89% B 90%

: 321851-63-2
(4R,5S)-3-[(2S)-2-{(2S)-N-benzyloxycarbonylpyrrolidin-2-yl}propanoyl]-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 235084-93-2
(2S)-2-[(2S)-1-benzyloxycarbonylpyrrolidin-2-yl]-1-propanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; water at 5℃; for 15h;	A 97 mg B 88%

: 133645-51-9
(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3"-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 133565-40-9
<1R-(1α,2β,7aα)>-Hexahydro-1-hydroxy-2-methyl-3-oxo-1H-pyrrolizine

Conditions

Conditions	Yield
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3"-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With trifluoroacetic acid at 20℃; for 0.333333h; Stage #2: With potassium carbonate In ethanol; water at 0℃; for 1.5h;	A n/a B 86%

: 80719-70-6
(4R,5S)-3-<(2S)-1-oxo-2,4-dimethylpent-4-enyl>-4-methyl-5-phenyloxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 82507-47-9
(S)-(-)-2,4-dimethylpent-4-en-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.0833333h;	A n/a B 85%

: 37577-28-9
(1S,2R)-(+)-norphedrine

: tetraethylammonium peroxycarbonate

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (1S,2R)-(+)-norphedrine; tetraethylammonium peroxycarbonate In acetonitrile at 20℃; for 2h; Acylation; Stage #2: With p-toluenesulfonyl chloride In acetonitrile at 25℃; for 10h; Cyclization;	85%

: 124-38-9
carbon dioxide

: 37577-28-9
(1S,2R)-(+)-norphedrine

: 98-59-9
p-toluenesulfonyl chloride

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 58107-41-8, 58107-43-0, 108591-33-9, 131142-88-6, 143957-01-1, 136173-99-4
N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]-4-methylbenzenesulfonamide

Conditions

Conditions	Yield
Stage #1: (1S,2R)-(+)-norphedrine In acetonitrile at 20℃; Electrolysis; Stage #2: carbon dioxide for 1h; Stage #3: p-toluenesulfonyl chloride at 20℃;	A 85% B 14%

...Expand

: 37577-28-9
(1S,2R)-(+)-norphedrine

: 105-58-8
Diethyl carbonate

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With potassium carbonate In toluene at 110℃; Inert atmosphere; Large scale reaction;	84.3%
With potassium carbonate at 150℃; for 2.5h;	83%
MCM-41-TBD; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine for 24h; Heating;	59%

: 95798-32-6
(4R,5S)-3-<(2R)-1-oxo-2-<<(phenylmethyl)thio>methyl>-3-phenylpropyl>-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 95841-15-9
(2R)-2-<<(phenylmethyl)thio>methyl>-3-phenylpropanoic acid benzyl ester

Conditions

Conditions	Yield
With lithium benzyloxide In tetrahydrofuran; hexane at 0℃; for 1.5h;	A 75% B 83%

: 954106-16-2
C21H29NO3

A: 179913-85-0
(2R,3S)-2,3,7-trimethyl-6-octen-1-ol

B: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 5h;	A 81% B 83%

: C17H23NO3

: 6148-64-7
ethyl potassium malonate

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 874208-98-7
ethyl (R)-5-methyl-3-oxo-octanoate

Conditions

Conditions	Yield
Stage #1: C17H23NO3; ethyl potassium malonate With triethylamine; magnesium chloride In acetonitrile at 80℃; for 20h; Stage #2: With hydrogenchloride In water at 10℃; Further stages.;	A n/a B 83%

...Expand

: 80697-95-6
(4R,5S)-4-methyl-3-((S)-2-methylpent-4-enoyl)-5-phenyloxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 5673-98-3, 63501-27-9, 88080-30-2, 63501-26-8
(S)-(-)-2-methyl-4-penten-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran -70 deg C, 40 min; -78 deg C, 1 h; -78 to -20 deg C, 2 h;	A n/a B 82%

: 492-39-7
(1S,2S)-2-amino-1-phenylpropanol

: 105-58-8
Diethyl carbonate

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With potassium carbonate In toluene at 130℃; Heating;	80%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 134440-87-2
(2'R,3'S,4R,5S)-3-(3'-hydroxy-2'-methyl-4'-phenylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 184354-37-8
(2R,3S)-3-hydroxy-2-methyl-4-phenylbutan-(N-methyl-O-methyl)-hydroxamide

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 0 - 4℃; for 3h;	A n/a B 78%

...Expand

: 317801-57-3
(4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 317801-61-9
(R)-(+)-2-isopropyl-5-methylhex-5-ene-1-carboxylic acid

Conditions

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 16h; cleavage;	A n/a B 75%

: 124-38-9
carbon dioxide

: 37577-28-9
(1S,2R)-(+)-norphedrine

: 814-49-3
diethyl chlorophosphate

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: diethyl ((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)phosphoramidate

Conditions

Conditions	Yield
With tetramethylphenylguanidine In acetonitrile at -40 - 20℃;	A 55% B n/a
With N,N,N',N'-tetramethyl-N-phenylguanidine In acetonitrile at -40 - 25℃;	A 55% B 22%

...Expand

: 125453-11-4
benzyl N-(1H-benzotriazol-1-ylmethyl)carbamate

: 96930-16-4
(4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: [(S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-2-phenyl-propyl]-carbamic acid benzyl ester

C: [(R)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-2-phenyl-propyl]-carbamic acid benzyl ester

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	A 20% B 54% C 2%

...Expand

: 96930-16-4
(4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: [(S)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-2-phenyl-propyl]-carbamic acid benzyl ester

C: [(R)-3-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-2-phenyl-propyl]-carbamic acid benzyl ester

Conditions

Conditions	Yield
With benzyl N-(1H-benzotriazol-1-ylmethyl)carbamate; lithium diisopropyl amide In tetrahydrofuran	A 20% B 54% C 2%

...Expand

: 142719-20-8
Acetic acid (1S,2R)-1-ethyl-2-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl ester

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 142719-21-9
(2S,3R,6R,7S)-7-Ethyl-3,6-dimethyl-2-phenyl-1,8-dioxa-4-aza-cycloundecane-5,9,11-trione

C: 142761-27-1
(5R,6S)-6-Ethyl-4-hydroxy-5-methyl-5,6-dihydro-pyran-2-one

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h;	A 45% B 43% C 37%

...Expand

: 1147550-11-5
ammonium thiocyanate

: 40626-29-7
Acutrim

A: 4-methyl-5-phenyl-thiazolidin-2-one

B: (4R,5R)-(+)-4-methyl-5-phenyl-thiazolidin-2-one

C: (4R,5S)-4-Methyl-5-phenyl-thiazolidine-2-thione

D: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
at 180 - 200℃; for 4h; Further byproducts given;	A n/a B 40% C n/a D n/a

...Expand

: 317801-57-3
(4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone

A: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

B: 264258-71-1
(R)-(+)-2-isopropyl-5-methylhex-5-en-1-ol

C: (2R)-N-2-((1S,2R)-2-methyl-1-phenylethoxy)-5-methyl-2-(1-methylethyl)-5-hexenyl amide

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 0℃; Reduction;	A 25% B 33% C 39%

...Expand

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 849488-05-7
(R)-6-cyclohexyl-4-methylhexanoic acid

: (4R,5S)-3-((R)-6-cyclohexyl-4-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (R)-6-cyclohexyl-4-methylhexanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-methyl-5-phenyloxazolidin-2-one With lithium chloride In tetrahydrofuran at 0 - 20℃;	100%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 39716-58-0
pent-4-enoyl chloride

: 96930-18-6
(4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	99%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere;	99%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.583333h; Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at -78 - -20℃; Further stages.;	86%
With n-butyllithium 1.) THF, -78 deg C, 1 h, 2.) 20 deg C, 24 h; Yield given. Multistep reaction;

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 57679-86-4, 70173-09-0
(Z)-Dec-4-enoyl chloride

: 118267-98-4
(4R,5S)-3-((Z)-Dec-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - -10℃;	99%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 75-36-5
acetyl chloride

: 96093-41-3
(4R,5S)-3-acetyl-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃;	99%
With n-butyllithium In tetrahydrofuran 1.) -78 deg C, 20 min, 2.) r.t., 20 min;	90%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 141-75-3
butyryl chloride

: 80697-91-2
(4R,5S)-(+)-4-methyl-3-(1'-oxobutyl)-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane Stage #2: butyryl chloride In tetrahydrofuran; hexane at 20℃; for 2h;	99%
With n-butyllithium In tetrahydrofuran at -78℃;	91%
With n-butyllithium 1.) THF, -78 deg C, 1 h, 2.) 20 deg C, 24 h; Yield given. Multistep reaction;

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 108-12-3
isopentanoyl chloride

: 107599-99-5
(4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane Stage #2: isopentanoyl chloride In tetrahydrofuran; hexane at 20℃; for 2h;	99%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: isopentanoyl chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	99%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: isopentanoyl chloride In tetrahydrofuran; hexachloroethane at -78℃; for 0.5h;	39%
With n-butyllithium 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 30 min; Yield given. Multistep reaction;
With n-butyllithium In tetrahydrofuran at -78 - 20℃;

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 31819-97-3
1-iodo-2,2-dimethyl-1,2-propadiene

: (4R,5S)-4-Methyl-3-(3-methyl-buta-1,2-dienyl)-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
With potassium phosphate; copper(I) thiophene-2-carboxylate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In toluene at 85℃; for 5h;	99%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 104-97-2
cyclopentanepropanoyl chloride

: 944385-34-6
(4R,5S)-3-(3-cyclopentylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h;	99%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 79-03-8
propionyl chloride

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	98%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane Stage #2: propionyl chloride In tetrahydrofuran; hexane at 20℃; for 2h;	98%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran; hexane at -78 - -50℃; for 2h;	98%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 79-30-1
isobutyryl chloride

: (4R,5S)-3-isobutyryl-4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h; deprotonation; Stage #2: isobutyryl chloride In tetrahydrofuran at -78℃; for 2h; Acylation;	98%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 142-61-0
Hexanoyl chloride

: 131636-15-2
(4R,5S)-3-hexanoyl-4-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	97%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: Hexanoyl chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; water	72%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane; ethyl acetate at -78℃; for 0.166667h; Stage #2: Hexanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;	72%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 123-62-6
propionic acid anhydride

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

Conditions

Conditions	Yield
With electrogenerated base from 2-pyrrolidone; tetraethylammonium perchlorate In acetonitrile at 20℃;	97%
With dmap; triethylamine In tetrahydrofuran for 1h; Ambient temperature;	73%
With 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine In chloroform-d1 at 50℃; for 3h; Inert atmosphere;

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 38136-29-7
4-methylvaleroyl chloride

: 134458-52-9
(4R,5S)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.25h; Inert atmosphere; Stage #2: 4-methylvaleroyl chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	97%
With n-butyllithium; sodium hydrogencarbonate In tetrahydrofuran; hexanes at -78 - 0℃; for 1.41667h; Argon atmosphere;	82%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: 4-methylvaleroyl chloride In tetrahydrofuran; hexane at -78℃; for 0.5h;	38%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 610300-44-2
3-(4,4-dimethyl-heptanoyl)-(R)-4-methyl-(S)-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4,4-dimethyl-heptanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-methyl-5-phenyloxazolidin-2-one With lithium chloride In tetrahydrofuran for 18h;	95%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 50902-80-2
4,4-dimethyl-heptanoic acid

: 610300-44-2
3-(4,4-dimethyl-heptanoyl)-(R)-4-methyl-(S)-5-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 4,4-dimethyl-heptanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran for 1h; Stage #2: 4-methyl-5-phenyloxazolidin-2-one With lithium chloride In tetrahydrofuran for 18h;	95%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 1174281-26-5
3-cyano-4,6-dimethyl-2-pyridinyl tosylate

: 1233503-31-5
4,6-dimethyl-2-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidin-3-yl)nicotinonitrile

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	95%

: 922724-77-4
4-(2-propenyloxy)butanoyl chloride

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 922724-76-3
(4R)-methyl-(5S)-phenyl-3-(4-propenyloxy)butanoyloxazolidin-2-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran for 0.5h; cooling;	94%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 625-35-4, 3488-22-0, 10487-71-5
trans-chrotonyl chloride

: 90719-31-6
(4R,5S)-3-((E)-2-butenoyl)-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, -78 deg C, 15 min; 2.) THF, -78 deg C, 30 min then 0 deg C, 15 min;	93%
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With n-butyllithium In tetrahydrofuran at -40℃; Stage #2: trans-chrotonyl chloride In tetrahydrofuran at -50℃; Further stages.;

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 35928-65-5
(methylthio)acetyl chloride

: 116857-38-6
(4R,5S)-3-(1'-oxo-2'-methylthioethyl)-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) r.t., 30 min;	93%
	77%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 108-24-7
acetic anhydride

: 96093-41-3
(4R,5S)-3-acetyl-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
Stage #1: 4-methyl-5-phenyloxazolidin-2-one With tetraethylammonium perchlorate In acetonitrile at 20℃; Electrochemical reaction; Stage #2: acetic anhydride With tetraethylammonium perchlorate In acetonitrile at 20℃; for 3h; Further stages.;	93%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 383397-31-7
4-triethylsilyloxy-4-methylpentanoic acid

: 383397-33-9
(4R,5S)-(+)-4-methyl-5-phenyl-3-[4-triethylsilyloxy-4-methylpentanoyl]-2-oxazolidinone

Conditions

Conditions	Yield
With dmap; pivaloyl chloride; triethylamine	93%

: 77943-39-6
4-methyl-5-phenyloxazolidin-2-one

: 2111-53-7
(S)-(-)-citronellic acid

: 954106-37-7
(4R,5S)-3-(3,7-dimethyloct-6-enoyl)-4-methyl-5-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
With dmap; pivaloyl chloride; triethylamine In tetrahydrofuran for 24h; Heating;	93%

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone Specification

The (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone with the CAS number 77943-39-6 is also called 2-Oxazolidinone,4-methyl-5-phenyl-, (4R,5S)-. Both the systematic name and IUPAC name are (4R,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one. Its molecular formula is C₁₀H₁₁NO₂. This chemical belongs to the following product categories: (1)Chiral; (2)Peptide. While using this chemical, you should not breathe dust and avoid it contact with skin and eyes.

The properties of the (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone are: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 15.88; (6)ACD/BCF (pH 7.4): 15.88; (7)ACD/KOC (pH 5.5): 251.93; (8)ACD/KOC (pH 7.4): 251.93; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.526; (14)Molar Refractivity: 48.07 cm³; (15)Molar Volume: 156.4 cm³; (16)Polarizability: 19.05×10^-24cm³; (17)Surface Tension: 36.3 dyne/cm; (18)Enthalpy of Vaporization: 64.6 kJ/mol; (19)Vapour Pressure: 1.79×10^-6 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2O[C@@H](c1ccccc1)[C@H](N2)C
(2)InChI: InChI=1/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
(3)InChIKey: PPIBJOQGAJBQDF-VXNVDRBHBU

Product Name

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Synthetic route

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone Specification

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