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247068-82-2

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Basic Information

Molecular Structure:
CAS No.:	247068-82-2
Name:	CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
Article Data:	32

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

Synthetic route

: tert-butyl {(1S,2S)-1-hydroxy-4-methyl-1-[(R)-2-methyloxiran-2-yl]pentan-2-yl}carbamate

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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℃;

: 247068-81-1
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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 ((R)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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%

: 1609959-47-8
tert-butyl N-[(2S)-1-(-2-methyloxirane-2-yl)-1-hydroxy-4-methylpentan-2-yl]carbamate

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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

: 247068-81-1
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate

A: tert-butyl ((S)-4-methyl-1-((S)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate

B: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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;

: 24424-99-5
di-tert-butyl dicarbonate

: (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 13h;	39%

: 1186298-17-8
(1-isobutyl-3-methyl-2-oxo-but-3-enyl)carbamic acid tert-butyl ester

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
With 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In water; acetonitrile at -10℃; Inert atmosphere;	38%

: 87694-50-6
N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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

: 13139-15-6
N-tert-butoxycarbonyl-L-leucine

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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

: 1609959-45-6
tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate

: 247068-82-2
tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions	Yield
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

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