Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate at 120 - 130℃; for 3h; | 100% |
With potassium carbonate In ethanol at 130 - 135℃; for 1h; | 88% |
With potassium carbonate at 135 - 140℃; for 2h; | 84% |
(4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one
A
(R)-3-phenyl-3-aminopropionic acid
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With Pearlman's catalist; hydrogen In methanol at 20℃; for 24h; | A 43% B 100% |
(S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one
A
(S)-4-Benzyl-2-oxazolidinone
B
(2S,4S)-2-Azido-4-methyl-hexanoic acid
Conditions | Yield |
---|---|
Stage #1: (S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h; Stage #2: With hydrogenchloride In water pH=1 - 2; | A 99% B 96.7% |
methanol
(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone
A
methyl (2R)-2-methyl-3-phenylpropanoate
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 20℃; for 72h; | A 98% B 99% |
ethanol
(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone
A
ethyl laurate
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 20℃; for 168h; | A 99% B 99% |
(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone
benzyl alcohol
A
benzyl dodecanoate
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 20℃; for 168h; | A 83% B 99% |
(S)-4-benzyl-3-propionyl-2-oxazolidinone
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With methanol; C17H23BN2O at 25℃; under 760.051 Torr; for 1h; Inert atmosphere; chemoselective reaction; | 98% |
Multi-step reaction with 2 steps 1: 1.) di-n-butylboron triflate, N,N-diisopropylethylamine, 3.) aq. H2O2 / 1) CH2Cl2, 0 deg C, 30 min; 2) CH2Cl2, -78 deg C, 45 min, 0 deg C, 2 h; 3) methanol, 0 deg C, 1 h 2: 1.) trimethylaluminum / 1) CH2Cl2, toluene, rt, 1 h; 2) CH2Cl2, toluene, -20 deg C --> rt, rt, 1.5 h View Scheme | |
Multi-step reaction with 2 steps 1: 1.) dibutylboron trifluoromethanesulfonate, diisopropylethylamine / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, -78 deg C (1 h), room temp. (5 h) 2: 80 percent / LiBH4, H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 98% B 96% |
N-(4-benzyl-2-oxo-oxazolidin-3-yl)-N-(5-chloro-1-propyl-pentyl)-benzamide
A
N-(5-chloro-1-propyl-pentyl)-benzamide
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.166667h; | A 97% B n/a |
tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate
A
(3R)-2-[3-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water for 3h; | A 97% B 89% |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 97% B n/a |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 97% B n/a |
(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone
A
2-methyl-3-phenylpropionic acid
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone With ytterbium(III) triflate In methanol for 3h; Stage #2: With lithium hydroxide In tetrahydrofuran; water for 2h; | A 97% B 97% |
(S)-ethyl (1-hydroxy-3-phenylpropan-2-yl)carbamate
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With potassium carbonate In toluene for 3h; Heating; | 96% |
With potassium carbonate at 100 - 130℃; | |
With hydrotalcite; magnesium aluminum In toluene at 110℃; for 5h; | 91 % Spectr. |
With potassium carbonate at 125 - 130℃; under 33.7534 - 37.5038 Torr; | |
With polyethylene glycol 400(PEG-400) In toluene Reflux; Large scale; | 167 kg |
(4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclopentyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one
A
(S)-4-Benzyl-2-oxazolidinone
B
(1S,2S)-2-methyl-1-(1-phenylsulfanylcyclopentyl)propane-1,3-diol
Conditions | Yield |
---|---|
With lithium borohydride; water In tetrahydrofuran for 3h; Ambient temperature; | A 80% B 96% |
Conditions | Yield |
---|---|
With sodium acetate; palladium diacetate In acetonitrile at 20℃; under 760 Torr; Electrolysis; | 96% |
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating; | 88% |
With oxygen; copper-(N-heterocyclic carbene) complex In 1,4-dioxane at 100℃; under 37503.8 Torr; for 3h; | 86% |
ethyl 1-imidazolecarboxylate
L-Phenylalaninol
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 15h; Reflux; | 96% |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 96% B n/a |
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.0833333h; | 95% |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 95% B n/a |
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With pyrrolidine In acetonitrile at 55℃; for 4.5h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With sodium methylate In dichloromethane at 20℃; for 4h; | A 92% B n/a |
N-benzyloxyamine
(S)-3-benzoyl-4-phenylmethyl-2-oxazolidinone
A
N-benzyloxy benzamide
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With samarium(III) trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.5h; | A 91% B n/a |
methanol
A
(S)-4-Benzyl-2-oxazolidinone
B
(2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate
Conditions | Yield |
---|---|
With C17H23BN2O at 25℃; under 760.051 Torr; for 48h; Inert atmosphere; chemoselective reaction; | A 91% B 89% |
(4S)-4-benzyl-1,3-oxazolidine-2-thione
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With methyloxirane In chloroform at 150℃; for 1h; Inert atmosphere; Microwave irradiation; | 90% |
With sodium hydroxide; dihydrogen peroxide In water Ambient temperature; | 56% |
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide for 0.0333333h; Cyclization; microwave heating; | 90% |
Conditions | Yield |
---|---|
With caesium carbonate In dimethylsulfoxide-d6 at 25 - 150℃; under 2280.15 Torr; for 24h; Schlenk technique; Autoclave; | 90% |
Stage #1: carbon dioxide; L-Phenylalaninol 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.; | 71% |
With Hexamethylcyclotrisiloxane; tetrabutyl ammonium fluoride In dimethylsulfoxide-d6 at 150℃; under 760.051 Torr; for 9h; Reagent/catalyst; chemoselective reaction; | 78 %Spectr. |
L-Phenylalaninol
mononitrophenyl carbonate
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With dmap In dichloromethane for 3h; | 90% |
(S,E)-4-benzyl-3-(3-oxobut-1-en-1-yl)oxazolidin-2-one
1-dodecylthiol
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 0.3h; Inert atmosphere; | A n/a B 90% |
B
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 2h; | A 89.2% B 1.05 g |
With sodium tetrahydroborate; water In tetrahydrofuran at 20 - 40℃; for 2h; | A 89.2% B 1.05 g |
(S)-4-Benzyl-2-oxazolidinone
propionyl chloride
(S)-4-benzyl-3-propionyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: propionyl chloride In tetrahydrofuran at 0 - 20℃; | 100% |
With n-butyllithium In tetrahydrofuran | 100% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 99% |
(S)-4-Benzyl-2-oxazolidinone
propionic acid
(S)-4-benzyl-3-propionyl-2-oxazolidinone
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 100% |
With 2-chloro-1-methylpyridinium p-toluenesulfonate; triethylamine In dichloromethane at 20℃; for 7h; | 94.4% |
With triethylamine In tetrahydrofuran | 80% |
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran | |
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran |
(S)-4-Benzyl-2-oxazolidinone
isopentanoyl chloride
(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium; triphenylmethane In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: isopentanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Stage #3: With potassium carbonate In tetrahydrofuran; hexane; water | 100% |
With triethylamine; dmap In dichloromethane at 0 - 10℃; for 0.5h; | 95% |
With dmap In dichloromethane; water at 0 - 10℃; for 0.5h; | 95% |
di-tert-butyl dicarbonate
(S)-4-Benzyl-2-oxazolidinone
(S)-3-(tert-butoxycarbonyl)-4-benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With dmap In acetonitrile at 25℃; for 0.116667h; | 100% |
pent-4-enoyl chloride
(S)-4-Benzyl-2-oxazolidinone
(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With n-butyllithium | 100% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 99% |
With n-butyllithium In tetrahydrofuran at -78 - 20℃; | 97% |
(S)-4-Benzyl-2-oxazolidinone
3-[dimethyl(phenyl)silyl]glutaric anhydride
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; for 24h; | 100% |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane 1.) -35 deg C, 10 min, 2.) -78 deg C, 1 h; | 100% |
With dmap In dichloromethane at 20℃; |
(S)-4-Benzyl-2-oxazolidinone
2-Bromoacetyl bromide
4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone
Conditions | Yield |
---|---|
With n-butyllithium at -78 - 20℃; for 0.5h; | 100% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78 - 20℃; for 16.5h; Inert atmosphere; | 92% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.5h; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78℃; for 1h; | 87% |
6-bromohexanoic acid
(S)-4-Benzyl-2-oxazolidinone
(S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 6-bromohexanoic acid In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 100% |
With n-butyllithium; pivaloyl chloride; triethylamine Multistep reaction; | |
Stage #1: 6-bromohexanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -78 - 0℃; Stage #2: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; |
(S)-4-Benzyl-2-oxazolidinone
(S)-3-amino-4-benzyl-1,3-oxazolan-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With potassium hydride Stage #2: With chloroamine In tert-butyl methyl ether | 100% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In 1,4-dioxane; mineral oil at 60℃; for 1h; Stage #2: In 1,4-dioxane; mineral oil at 20℃; for 6h; | 86% |
With n-butyllithium; O-(diphenylphosphinyl)hydroxylamine In tetrahydrofuran; hexane at 20℃; for 6h; | 80% |
(S)-4-Benzyl-2-oxazolidinone
Cinnamic acid
(S)-4-benzyl-3-(6-(benzyloxy)hex-2-enoyl)oxazolidin-2-one
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 100% |
cyclopentanepropanoyl chloride
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane | 100% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; | 100% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; | 90% |
4-bromobutyroyl chloride
(S)-4-Benzyl-2-oxazolidinone
(S)-4-benzyl-3-(4-bromobutanoyl)oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromobutyroyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 100% |
(S)-4-Benzyl-2-oxazolidinone
valeric acid
3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10 - 15℃; for 2h; Large scale; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride at 20℃; Large scale; | 100% |
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -20 - -15℃; for 1h; Inert atmosphere; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at -20 - 20℃; for 16h; Solvent; Temperature; Reagent/catalyst; | 98.12% |
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at 20 - 25℃; for 16h; | 94% |
(S)-4-Benzyl-2-oxazolidinone
n-valeryl chloride
3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -70 - -65℃; for 0.5h; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran at -75 - -65℃; for 1h; | 99.9% |
With dmap; triethylamine In dichloromethane at 0 - 10℃; for 3h; Large scale; | 98% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; | 95% |
(S)-4-Benzyl-2-oxazolidinone
acetyl chloride
(S)-3-acetyl-4-benzyloxazolidin-2-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at 0℃; | 99% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 94.5% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran Inert atmosphere; Stage #2: acetyl chloride at -78℃; for 0.5h; Inert atmosphere; | 82% |
(S)-4-Benzyl-2-oxazolidinone
butyryl chloride
(S)-4-benzyl-3-butyryloxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: butyryl chloride In tetrahydrofuran at -78℃; for 3h; | 99% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: butyryl chloride In tetrahydrofuran at -78 - 20℃; for 2.25h; | 98% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: butyryl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3.67h; | 98% |
(S)-4-Benzyl-2-oxazolidinone
α-allyloxyacetyl pivaloyl anhydride
(4S)-3-(2-allyloxyethanoyl)-4-benzyloxazolidin-2-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 99% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: α-allyloxyacetyl pivaloyl anhydride In tetrahydrofuran; hexane at -78 - 0℃; for 0.75h; Further stages.; | 5.45 g |
With n-butyllithium In tetrahydrofuran; diethyl ether at -78 - 0℃; for 0.75h; | 10.0 g |
(S)-4-Benzyl-2-oxazolidinone
(S)-3-<1-oxo-2-(but-3-enyl-1-oxy)>-4-benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 99% |
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction; |
(S)-4-Benzyl-2-oxazolidinone
(S)-3-<1-oxo-2-(pent-4-enyl-1-oxy)>-4-benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 99% |
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction; |
(S)-4-Benzyl-2-oxazolidinone
phenylacetaldehyde
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In toluene Reflux; Dean-Stark; | 99% |
With 1,2,3-Benzotriazole; toluene-4-sulfonic acid In toluene for 48h; Heating; | 62% |
(S)-4-Benzyl-2-oxazolidinone
phenylbutyric acid chloride
(S)-4-benzyl-3-(3-phenylbutanoyl)oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h; | 99% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h; | 99% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran at -78 - 0℃; for 3.5h; | 99% |
With n-butyllithium 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT; Yield given; Multistep reaction; | |
With n-butyllithium; triphenylmethane In tetrahydrofuran at -78℃; |
4-Cyanochlorobenzene
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; johnphos In toluene at 115℃; for 15h; | 99% |
With potassium phosphate; [(π-allyl)Pd(tBuBrettPhos)]OTf In tert-butyl alcohol at 110℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube; | 95% |
With (PAd2-DalPhos)NiCl(o-tol); caesium carbonate In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; | 64% |
(S)-4-Benzyl-2-oxazolidinone
n-valeryl chloride
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; ethyl acetate | 99% |
(S)-4-Benzyl-2-oxazolidinone
3-cyclohexylpropionyl chloride
(4S)-3-(3-cyclohexyl-1-oxopropyl)-4-phenylmethyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 99% |
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran at -78 - 20℃; |
IUPAC Name: (4S)-4-benzyl-1,3-oxazolidin-2-one
Synonyms of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): (S)-(-)-4-Benzyl-2-oxazolidinone
CAS NO: 90719-32-7
Molecular formula: C10H11NO2
Molecular Weight: 177.2
Molecular Structure:
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.551
Molar Refractivity: 48.08 cm3
Molar Volume: 150.5 cm3
Surface Tension: 43.2 dyne/cm
Density: 1.176 g/cm3
Flash Point: 195 °C
Enthalpy of Vaporization: 64.95 kJ/mol
Boiling Point: 398.8 °C at 760 mmHg
Vapour Pressure: 1.43E-06 mmHg at 25°C
Melting point: 86-88 °C(lit.)
Alpha: -62 o (C=1, CHCl3)
Storage temp: 0-6°C
Sensitive: Hygroscopic
Appearance: white to light yellow crystal powder
Product Categories of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): Oxazolidinone;Chiral Compounds;chiral;Aromatics Compounds;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Aromatics;Chiral Reagents;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
(S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7) is a kind of pharmaceutical intermediate.
Safety Information about (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 3-10
HS Code: 29349990
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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