115887-91-7

Basic information

• Product Name: sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate
• CAS NO: 115887-91-7
• Molecular Formula: C₁₂H₁₃N₂O₆S*Na
• Molecular Weight: 336.29619
• Mol File: 115887-91-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate(115887-91-7)
• EPA Substance Registry System: sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate(115887-91-7)

Safety Data

• Hazardous Substances Data: 115887-91-7(Hazardous Substances Data)

Usage

General Description

Sodium (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonate is a complex chemical compound with numerous applications in different industrial and scientific sectors. As an organic sodium salt, it is formed from the reaction of an equivalent amount of sodium and (2S,3S)-3-(benzyloxycarbonylamino)-2-methyl-4-oxo-azetidine-1-sulfonic acid. The presence of the azetidine ring, a four-membered cyclic amine, gives this compound unique chemical properties and reactivity. The structure also contains a carbonyl group, a sulfonic acid ester and a benzyl group. Detailed information about physical properties such as melting point, boiling point, and solubility are generally determined by specific lab analysis. As with any chemical, safety precautions should be noted when handling this substance due to its potential hazards. Its specific use would depend on the nature of the research or application.

Synthetic route

N-sulfo-N-benzyloxycarbonyl-O-methanesulfonyl-L-threonine amide → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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 (115887-89-3) → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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 (115764-26-6) → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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 (115935-89-2) → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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

C13H18N2O9S2 → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
With sodium carbonate In water pH=8.25 - 8.35; Large scale;	50 kg

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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 (49705-98-8) → (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7)

Conditions	Yield
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 (115887-91-7) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
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;

Upstream product

• 49705-98-8 benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 115935-89-2 (3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115764-26-6 (3S,4R)-3-benzyloxycarbonylamino-4-mesyloxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115887-89-3 (3S,4R)-3-benzyloxycarbonylamino-4-iodomethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 80082-62-8 (2R,3S)-3-Benzyloxycarbonylamino-2-methyl-4-oxo-azetidine-1-sulfonatetetrabutyl-ammonium; 

Downstream Products

• 80082-65-1 (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid 
• 80082-65-1 cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid 

Relevant articles and documents

Preparation method of amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate

The invention discloses a preparation method of an amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate, comprising the following steps: S1, adding N-carbobenzoxy-L-threonine amide into a reaction vessel, adding an organic solvent, stirring, mixing, adding 2-methylpyridine and methylsulfonyl chloride, heating, and carrying out a thermal reaction to obtain a reaction solution I; S2, cooling the reaction solution I to below 0 DEG C, then adding chlorosulfonic acid into the cooled reaction solution I, heating, carrying out a thermal reaction to obtain a reaction solution II, and cooling; and S3, adding deionized water into the cooled reaction solution II for a quenching reaction, then adding alkali liquor into the reaction system to adjust the pH, heating, and carrying out a thermal reaction. The method adopts a one-pot method for synthesis, is simple in process operation and short in period, avoids the generation of three wastes, and realizes the production of a green process; thepurity of the obtained amino-2-methyl-4-oxo-1-azetidinesulfonic acid intermediate is as high as 98.5%, the molar yield is as high as 80.9%, the product quality is good, and the method is suitable forindustrial production.

Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains

Disclosed herein are processes for preparing a compound of the formula STR1 in which a novel compound of the formula STR2 is reacted with a beta lactam of the formula STR3 by treatment with a base, wherein the symbols are as defined in the specification.

Enantioselective Synthesis of (3S)-trans-4-(Substituted Methyl)monobactams from 2,3-O-Isopropylidene-D-glyceraldehyde

The enantioselective synthesis of various (3S)-trans-4-(substituted methyl)-2-oxoazetidine-1-sulphonic acid derivatives from 2,3-O-isopropylidene-D-glyceraldehyde is described.Reaction of this aldehyde with trimethylsilyl cyanide gave a 80:20 ratio of the corresponding threo and erythro α-amino-nitriles, which by amino protection and subsequent treatment with basic hydrogen peroxide provided the corresponding α-amino carboxamides.Successive selective protection, activation, sulphonation and, finally, stereospecific cyclization of the threo α-carboxamide yielded (2S,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid, an intermediate for the synthesis of the corresponding 4-acyloxymethyl-, 4-carbamoyloxymethyl-, 4-methylsulphonyloxy-methyl-, 4-iodomethyl-, and 4-methyl-2-oxozetidines.