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CAS No.: | 120205-50-7 |
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Name: | ((2R,3R)-3-((S)-1-(tertbutoxycarbonyl)pyrrolidin-2-yl)-3-Methoxy-2-Methylpropanoic acid |
Article Data: | 39 |
Molecular Structure: | |
Formula: | C14H25NO5 |
Molecular Weight: | 287.356 |
Synonyms: | ((2R,3R)-3-((S)-1-(Tertbutoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid; |
Density: | 1.133±0.06 g/cm3(Predicted) |
Boiling Point: | 397.8±17.0 °C(Predicted) |
PSA: | 76.07000 |
LogP: | 2.05950 |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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Stage #1: (S)-t-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-((R)-2-oxo-4-phenyloxazolidin-3-yl)propyl)pyrrolidine-1-carboxylate With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran at 0℃; for 3h; Stage #2: With sodium sulfite In tetrahydrofuran at 20 - 25℃; for 16h; | 99% |
(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h; Stage #2: With water; lithium hydroxide In tetrahydrofuran at 0℃; for 3h; | 98% |
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h; | 98% |
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h; Stage #2: With lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h; | 98% |
<2S-<2R*<(R*),α(S*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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With hydrogen; palladium on activated charcoal In methanol for 12h; Ambient temperature; | 94% |
ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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With lithium hydroxide In ethanol | 91% |
With lithium hydroxide In ethanol; water at 20℃; | 59% |
With lithium hydroxide In ethanol at 20℃; | 59% |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
methyl iodide
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 0℃; | 91% |
With sodium hydride In tetrahydrofuran at 0℃; for 18h; | 89% |
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid; methyl iodide With sodium hydride In tetrahydrofuran at -5 - 0℃; for 75h; Stage #2: With potassium hydrogensulfate In water pH=2; | 72% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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Stage #1: C24H34N2O6 With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran for 4h; Stage #2: With sodium thiosulfate In tetrahydrofuran | 91% |
tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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With lithium hydroxide In tetrahydrofuran; water at 20℃; for 16h; | 86% |
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
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With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetonitrile for 48h; | 81% |
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; acetonitrile at 20℃; for 72h; | 75% |
Multi-step reaction with 2 steps 1: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h 2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h View Scheme | |
Stage #1: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol for 12h; Stage #2: With sodium periodate; sodium permanganate In water; acetonitrile at 0 - 5℃; for 4h; | |
Multi-step reaction with 2 steps 1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 6 h / 20 °C 2: sodium periodate; potassium permanganate / water / 6 h / 0 °C View Scheme |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
A
N-Boc-(2R,3R,4S)-dolaproine
C
[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
Conditions | Yield |
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With sodium hydride; methyl iodide In tetrahydrofuran at 0℃; for 48h; | A 76% B 5.3% C 5.6% |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
methyl iodide
A
N-Boc-(2R,3R,4S)-dolaproine
C
[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
Conditions | Yield |
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With sodium hydride In tetrahydrofuran at 0℃; for 48h; | A 76% B 5.3% C 5.6% |