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CAS No.: | 115887-91-7 |
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Name: | sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C12H14N2O6S.Na |
Molecular Weight: | 336.301 |
Synonyms: | (2S-trans)-2-Methyl-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid monosodium salt;(2S-trans)-2-methyl-4-oxo-3-[[(phenylmethoxy) carbonyl]amino]-1-azetidinesulfonic acid,monosodium salt;Sodium(2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate; |
PSA: | 124.22000 |
LogP: | 1.38190 |
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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With sodium hydroxide In water at 2 - 80℃; for 4h; pH=9; Temperature; pH-value; | 80.8% |
(3S,4R)-3-benzyloxycarbonylamino-4-iodomethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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With Dowex 50 Wx4 resin; Na form; tri-n-butyl-tin hydride In tetrahydrofuran for 2h; Ambient temperature; |
(3S,4R)-3-benzyloxycarbonylamino-4-mesyloxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 50 percent / sodium iodide / acetonitrile / 3 h / Heating 2: tributyltin hydride, Dowex 50 Wx4 resin, Na form / tetrahydrofuran / 2 h / Ambient temperature View Scheme |
(3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 98 percent / pyridine / 1 h / -20 °C 2: 50 percent / sodium iodide / acetonitrile / 3 h / Heating 3: tributyltin hydride, Dowex 50 Wx4 resin, Na form / tetrahydrofuran / 2 h / Ambient temperature View Scheme |
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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With sodium carbonate In water pH=8.25 - 8.35; Large scale; | 50 kg |
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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Multi-step reaction with 4 steps 1: ammonia / methanol / Large scale 2: α-picoline / dichloromethane / Large scale 3: chlorosulfonic acid / Large scale 4: sodium carbonate / water / pH 8.25 - 8.35 / Large scale View Scheme |
benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
Conditions | Yield |
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Multi-step reaction with 3 steps 1: α-picoline / dichloromethane / Large scale 2: chlorosulfonic acid / Large scale 3: sodium carbonate / water / pH 8.25 - 8.35 / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: α-picoline / dichloromethane; toluene / 10 h / 35 °C 2: chlorosulfonic acid / 10 h / -5 - 45 °C 3: sodium hydroxide / water / 4 h / 2 - 80 °C / pH 9 View Scheme |
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt
(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
Conditions | Yield |
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With hydrogen; palladium on activated charcoal In methanol; water for 2h; Ambient temperature; | |
With nitrogen; palladium In methanol; water | |
With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol; water for 2h; pH=6.8 - 7; | |
Stage #1: (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt With 5%-palladium/activated carbon; hydrogen In methanol at 15℃; for 4h; Large scale; Stage #2: With hydrogenchloride In methanol; water at 0℃; for 6h; Large scale; |