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CAS No.: | 247068-82-2 |
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Name: | CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester |
Article Data: | 32 |
Molecular Structure: | |
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Formula: | C14H25NO4 |
Molecular Weight: | 271.357 |
Synonyms: | CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester;tert-butyl (S)-4-Methyl-1-((R)-2-Methyloxiran-2-yl)-1-oxopentan-2-ylcarbaMate;N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-CarbaMic acid, 1,1-diMethylethyl ester;Boc-L-leucine epoxyketone;[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carbamic acid 1,1-dimethylethyl ester;Boc-leucine-epoxyketone;Boc-LeuEK(tert-butyl (S)-4-Methyl-1-((R)-2-Methyloxiran-2-yl)-1-oxopentan-2-ylcarbaMate );[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carbamic |
EINECS: | -0 |
Density: | 1.061±0.06 g/cm3(Predicted) |
Boiling Point: | 369.8±37.0 °C(Predicted) |
PSA: | 67.93000 |
LogP: | 2.67470 |
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; Green chemistry; | 91% |
With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; Cooling with ice; | 83.3% |
With Dess-Martin periodane In dichloromethane at 0℃; for 3h; Dess-Martin Oxidation; Inert atmosphere; | 46% |
With sodium hypochlorite; 2-azatricyclo[3.3.1.13,7]decan-2-ol; sodium hydrogencarbonate In water; toluene at 0℃; for 5h; | 5.96 g |
With Dess-Martin periodane In dichloromethane at 20℃; |
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With (R)-La-BINOL; triphenylphosphine; tert-butyl alcohol In toluene at 20℃; for 0.5h; Solvent; | 85% |
With dihydrogen peroxide; benzonitrile; N-ethyl-N,N-diisopropylamine In methanol at 0℃; | 57% |
With tetramethyl ammoniumhydroxide; urea hydrogen peroxide adduct In methanol; benzonitrile at -10℃; for 20h; Reagent/catalyst; Solvent; Inert atmosphere; stereoselective reaction; | 40% |
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With 1,8-diazabicyclo[5.4.0]undec-7-ene In tert-butyl methyl ether at 20℃; for 12h; | 84% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tert-butyl methyl ether at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Large scale; diastereoselective reaction; | 79% |
tert-butyl N-[(2S)-1-(-2-methyloxirane-2-yl)-1-hydroxy-4-methylpentan-2-yl]carbamate
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With Dess-Martin periodane In dichloromethane at 0℃; for 10h; Inert atmosphere; | 52% |
With Dess-Martin periodane In dichloromethane at 0 - 20℃; Inert atmosphere; | |
With Dess-Martin periodane In acetonitrile at 0 - 30℃; for 3h; | 4.5 g |
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate
B
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With dihydrogen peroxide; benzonitrile; N-ethyl-N,N-diisopropylamine at 0 - 4℃; for 43h; Alkaline aqueous solution; | A 28% B 48% |
With i-PrEtN; dihydrogen peroxide In methanol; water; benzonitrile at 0 - 4℃; for 43h; Yield given; Yields of byproduct given; | |
Stage #1: tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate With C28H34F6MnN6O6S2; acetic acid In acetonitrile for 0.0833333h; Inert atmosphere; Stage #2: With dihydrogen peroxide In acetonitrile at -20℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
di-tert-butyl dicarbonate
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With triethylamine In dichloromethane at 0 - 20℃; for 13h; | 39% |
(1-isobutyl-3-methyl-2-oxo-but-3-enyl)carbamic acid tert-butyl ester
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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With 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In water; acetonitrile at -10℃; Inert atmosphere; | 38% |
N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 92 percent / diethyl ether / 2.5 h / -78 °C 2: H2O2, i-PrEtN / benzonitrile; H2O; methanol / 43 h / 0 - 4 °C View Scheme | |
Multi-step reaction with 2 steps 1: tetrahydrofuran / 6 h / 0 °C / Inert atmosphere 2: potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 6 h / 0 - 25 °C 2.1: sodium hydrogencarbonate 2.2: trifluoroacetone 2.3: 1 h / -10 °C View Scheme |
N-tert-butoxycarbonyl-L-leucine
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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Multi-step reaction with 3 steps 1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 3 h / 25 °C / Inert atmosphere 2: tetrahydrofuran / 6 h / 0 °C / Inert atmosphere 3: potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 1.2: 3 h / 25 °C 2.1: tetrahydrofuran / 6 h / 0 - 25 °C 3.1: sodium hydrogencarbonate 3.2: trifluoroacetone 3.3: 1 h / -10 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: isobutyl chloroformate; 4-methyl-morpholine / dichloromethane / -10 - 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine; dihydrogen peroxide / methanol / 2 h View Scheme |
tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 30 °C 2: Dess-Martin periodane / acetonitrile / 3 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 10 h / 0 °C / Inert atmosphere View Scheme |