sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate

Base Information

• Chemical Name: sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate
• CAS No.: 115872-80-5
• Molecular Formula: C₂₂H₂₂ClN₆O₁₂S₂*Na
• Molecular Weight: 685.024
• Mol file: 115872-80-5.mol

Synonyms:sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate

Chemical Property of sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate

There total 14 articles about sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

(3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone (101668-47-7) → sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate (115872-80-5)

Guidance literature:

With Dowex 50W (Na+); sulfur trioxide pyridine complex; In dichloromethane; N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1248/cpb.36.469

Reference yield:

(4S)-4-(methoxycarbonylmethyl)-azetidine-2-one (77881-95-9) → sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate (115872-80-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 90 percent / lithium borohydride / 1,2-dimethoxy-ethane / 2 h / 45 - 50 °C

2: 79 percent / boron trifluoride etherate / CH₂Cl₂ / 0.33 h / -20 °C

3: 1.) 1.6 M n-butyllithium, diisopropylamine, 2.) trimethylchlorosilane, 3.) isoamyl nitrite / 1.) hexane/THF, -78 deg C, 2.) hexane/THF, 30 min, -50 deg C, 3.) hexane/THF, -78 deg C, 3 h

4: 75 percent / hydrogen / platinum oxide / ethyl acetate / 8 h / Ambient temperature

5: 91 percent / dioxane / Ambient temperature

6: 94 percent / 1 N HCl / methanol / 2 h / 40 °C

7: triethylamine / dimethylformamide / Ambient temperature

8: 1 N HCl / methanol / 0.5 h / 0 - 5 °C

9: 80 percent / boron trifluoride etherate / diethyl ether / 1 h / Ambient temperature

10: 520 mg / hydrogen / 5 percent Pd/C / methanol / 2 h / Ambient temperature

11: 1.) diphosgene, DMF, triethylamine, 2.) triethylamine / 1.) CH₂Cl₂, 1 h, -25 - -20 deg C, 2.) CH₂Cl₂, 0 deg C

12: 81 percent / 1 N HCl / methanol / 4 h / Ambient temperature

13: 88 percent / 1.) sulfur trioxide*pyridine, 2.) Dowex 50W (Na+) / dimethylformamide; CH₂Cl₂ / 3 h / 50 °C

With hydrogenchloride; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; Dowex 50W (Na+); boron trifluoride diethyl etherate; hydrogen; sulfur trioxide pyridine complex; triethylamine; diisopropylamine; N,N-dimethyl-formamide; isopentyl nitrite; trichloromethyl chloroformate; platinum(IV) oxide; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.36.469

Reference yield:

(6R)-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one (86541-17-5) → sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate (115872-80-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) 1.6 M n-butyllithium, diisopropylamine, 2.) trimethylchlorosilane, 3.) isoamyl nitrite / 1.) hexane/THF, -78 deg C, 2.) hexane/THF, 30 min, -50 deg C, 3.) hexane/THF, -78 deg C, 3 h

2: 75 percent / hydrogen / platinum oxide / ethyl acetate / 8 h / Ambient temperature

3: 91 percent / dioxane / Ambient temperature

4: 94 percent / 1 N HCl / methanol / 2 h / 40 °C

5: triethylamine / dimethylformamide / Ambient temperature

6: 1 N HCl / methanol / 0.5 h / 0 - 5 °C

7: 80 percent / boron trifluoride etherate / diethyl ether / 1 h / Ambient temperature

8: 520 mg / hydrogen / 5 percent Pd/C / methanol / 2 h / Ambient temperature

9: 1.) diphosgene, DMF, triethylamine, 2.) triethylamine / 1.) CH₂Cl₂, 1 h, -25 - -20 deg C, 2.) CH₂Cl₂, 0 deg C

10: 81 percent / 1 N HCl / methanol / 4 h / Ambient temperature

11: 88 percent / 1.) sulfur trioxide*pyridine, 2.) Dowex 50W (Na+) / dimethylformamide; CH₂Cl₂ / 3 h / 50 °C

With hydrogenchloride; n-butyllithium; chloro-trimethyl-silane; Dowex 50W (Na+); boron trifluoride diethyl etherate; hydrogen; sulfur trioxide pyridine complex; triethylamine; diisopropylamine; N,N-dimethyl-formamide; isopentyl nitrite; trichloromethyl chloroformate; platinum(IV) oxide; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.36.469

upstream raw materials:

(3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone

2-<2-<(chloroacetyl)amino>-4-thiazolyl>-(Z)-2-<<(p-nitrobenzyloxycarbonyl)methoxy>imino>acetic acid

(4S)-4-(methoxycarbonylmethyl)-azetidine-2-one

(3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-1-tertbutyldimethylsilyl-2-azetidinone

Downstream raw materials:

Sodium; (2R,3S)-3-{2-(2-amino-thiazol-4-yl)-2-[(Z)-4-nitro-benzyloxycarbonylmethoxyimino]-acetylamino}-2-(2-methoxy-ethyl)-4-oxo-azetidine-1-sulfonate