(3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone
• CAS No.: 101668-60-4
• Molecular Formula: C₂₀H₃₂N₂O₄Si
• Molecular Weight: 392.571
• Mol file: 101668-60-4.mol

Synonyms:(3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

Chemical Property of (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

There total 10 articles about (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone 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: 80.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3S,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone (101668-61-5) → (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone (101668-60-4)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; for 1h; Ambient temperature;

DOI:10.1248/cpb.36.469

Reference yield:

(4S)-4-(methoxycarbonylmethyl)-azetidine-2-one (77881-95-9) → (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone (101668-60-4)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; boron trifluoride diethyl etherate; hydrogen; triethylamine; diisopropylamine; isopentyl nitrite; platinum(IV) oxide; 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) → (3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone (101668-60-4)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; n-butyllithium; chloro-trimethyl-silane; boron trifluoride diethyl etherate; hydrogen; triethylamine; diisopropylamine; isopentyl nitrite; platinum(IV) oxide; In 1,4-dioxane; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.36.469

upstream raw materials:

diazomethane

(3S,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

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

(6R)-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one

Downstream raw materials:

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

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

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

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