tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate

Base Information

• Chemical Name: tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate
• CAS No.: 289042-12-2
• Molecular Formula: C29H40FN3O6S
• Molecular Weight: 577.718
• Hs Code.: 2935909550
• UNII: 10S8DBZ6MG
• Nikkaji Number: J3.653.603I,J3.653.764G
• Mol file: 289042-12-2.mol

Synonyms:289042-12-2;tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate;CID 9916218;10S8DBZ6MG;tert-butyl 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;1,1-Dimethylethyl [(4R,6S)-6-[(E)-2-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;1,3-Dioxane-4-acetic acid, 6-((1E)-2-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinyl)ethenyl)-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R,6S);UNII-10S8DBZ6MG;1,3-Dioxane-4-acetic acid, 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R,6S)-;C29H40FN3O6S;SCHEMBL1978779;4S,6R Acetonide t-Butyl Ester;WIFPCEOJTKZGSA-UQECUQMJSA-N;MFCD08458343;Rosuvastatin calcium impurity F [EP];AKOS024463022;AC-3414;DS-7417;((4R,6S)-6-{(E)-2-[4-(4-Fluoro-phenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl]-vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid tert-butyl ester;(4R,6S)-6-[(1E)-2-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester;CS-0154317;J3.653.603I;J3.653.764G;F19330;Q-201797;ROSUVASTATIN CALCIUM IMPURITY F [EP IMPURITY];(3R,5S,E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine-5-yl]-3,5-[(propane-2,2-diyl)bisoxy]-6-heptenoic acid tert-butyl ester;(4R,6S)-6-[(1E)-2-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidiny;[2,2-Dimethyl-6beta-[2-[2-[methyl(methylsulfonyl)amino]-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-yl]vinyl]-1,3-dioxane-4beta-yl]acetic acid tert-butyl ester;t-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate;tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethanesulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-butyl 2-((4S,6R)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-Butyl-(+)7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylsulfonylamino)pyrimidine-5-yl]-(3R,5S)-dioxane-(E)-heptenate;Tert-Butyl[(4R,6S)-6-{(E)-2-[4-(4-Fluorophenyl)-2-[Methyl(Methylsulfonyl)Amino]-6-(Propan-2-Y1)Pyrimidin-5-Yl]Ethenyl}-2,2-Dimethyl-1,3-Dioxan-4-Yl]Acetate;tert-Butyl2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Chemical Property of tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate

Chemical Property:

• Appearance/Colour: White or off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 153-155°C
• Refractive Index: 1.545
• Boiling Point: 673.348 °C at 760 mmHg
• PKA: -0.43±0.10(Predicted)
• Flash Point: 361.028 °C
• PSA: 116.30000
• Density: 1.211 g/cm³
• LogP: 6.53790
• Storage Temp.: Inert atmosphere,2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 577.26218534
• Heavy Atom Count: 40
• Complexity: 985

Purity/Quality:

98%min. ^*data from raw suppliers

(4R,6S)-6-[(1E)-2-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-aceticAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=NC(=NC(=C1C=CC2CC(OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)N(C)S(=O)(=O)C
• Isomeric SMILES: CC(C)C1=NC(=NC(=C1/C=C/[C@@H]2C[C@@H](OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)N(C)S(=O)(=O)C
• Uses: (4R,6S)-6-[(1E)-2-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester (Rosuvastatin EP Impurity F) is a Rosuvastatin (R700500) intermediate as HMG-CoA reductase inhibitor.

Technology Process of tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate

There total 50 articles about tert-Butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate 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: 95.0%

dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate (1221497-92-2) + tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) → 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester (289042-12-2,1378943-63-5)

Guidance literature:

dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; In tetrahydrofuran; at -35 - 0 ℃; for 21h; Product distribution / selectivity;

Reference yield: 91.0%

[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester (380460-37-7) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester (289042-12-2,1378943-63-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; water; at -15 - 42 ℃; for 1h; Temperature; Inert atmosphere;

Reference yield: 89.0%

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide + tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) → 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester (289042-12-2,1378943-63-5)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 20 - 70 ℃; Concentration; Temperature; Inert atmosphere;

upstream raw materials:

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

N-{4-(4-fluorophenyl)-6-isopropyl-5-[(1-methyl-1H-benzo[d]imidazol-2-ylsulfonyl)methyl]pyrimidin-2-yl}-N-methylmethanesulfonamide

tributyl[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-ylmethyl]phosphonium bromide

N-(5-bromo-4-(4-fluorophenyl)-6-isopropylpyriinidin-2-yl)-N-methylmethanesulfonamide

Downstream raw materials:

rosuvastatin methylamine salt

{(4R,6S)-6-[(E)-2-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid

[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]ethenyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate 1,1-dimethylethylammonium

2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid methyl ester

Refernces

• 1、 -. "Rosuvastatin calcium intermediate compound". Paragraph 0137-0141; 0145-0146. . Retrieved 2020/10/14.
• 2、 -. "Preparation method of statins intermediate". Paragraph 0052-0055; 0062-0065; 0072-0075; 0082-0085. . Retrieved 2018/11/27.