3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester

Base Information

• Chemical Name: 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester
• CAS No.: 164033-52-7
• Molecular Formula: C₂₅H₃₁NO₇S
• Molecular Weight: 489.59
• Mol file: 164033-52-7.mol

Synonyms:

Chemical Property of 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester

There total 5 articles about 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester 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:

pivaloyloxy 6-oxopenicillanate (77819-78-4) → 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester (164033-52-7)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 0 °C

2: H₂ / (Ph₃P)3RhCl / CH₂Cl₂; ethyl acetate / 2 h / 1520 Torr

3: PhHgCl, DBU / acetonitrile / Ambient temperature

4: acetonitrile

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; phenylmercury(II) chloride; Wilkinson's catalyst; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.7164/antibiotics.48.399

Reference yield:

(2S,5R)-3,3-Dimethyl-7-oxo-6-[2-oxo-prop-(Z)-ylidene]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (84277-96-3) → 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester (164033-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / (Ph₃P)3RhCl / CH₂Cl₂; ethyl acetate / 2 h / 1520 Torr

2: PhHgCl, DBU / acetonitrile / Ambient temperature

3: acetonitrile

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; phenylmercury(II) chloride; Wilkinson's catalyst; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.7164/antibiotics.48.399

Reference yield:

6-aminopenicillanic acid pivaloyloxymethyl ester (25031-08-7) → 3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester (164033-52-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaNO₂, 2.) O₃ / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -10 deg C

2: CH₂Cl₂ / 0 °C

3: H₂ / (Ph₃P)3RhCl / CH₂Cl₂; ethyl acetate / 2 h / 1520 Torr

4: PhHgCl, DBU / acetonitrile / Ambient temperature

5: acetonitrile

With hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; phenylmercury(II) chloride; sodium nitrite; Wilkinson's catalyst; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.7164/antibiotics.48.399

upstream raw materials:

phenylacetyl chloride

pivaloyloxy 6-oxopenicillanate

Pivaloyloxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-oxo-propyl)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

(2S,5R)-3,3-Dimethyl-7-oxo-6-[2-oxo-prop-(Z)-ylidene]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Downstream raw materials:

2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester