Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester

Base Information

• Chemical Name: Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester
• CAS No.: 239103-26-5
• Molecular Formula: C₂₁H₂₀N₄O₆S
• Molecular Weight: 456.479

Synonyms:

Chemical Property of Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester

There total 12 articles about Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl 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:

1-Bromo-2-iodobenzene (583-55-1) → Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester (239103-26-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 66 percent / BINAP, NaOBu-t / Pd(DBA)3 / toluene / 80 °C

2: Bu₃SnF / Pd(Tol₃P)2Cl₂ / benzene / Heating

3: H₂ / Pd/C / ethyl acetate

4: Et₃N / CH₂Cl₂

5: TBAF / tetrahydrofuran

6: Et₃N / CH₂Cl₂ / 0 °C

7: DBU / 23 °C

8: K₂CO₃ / methanol; H₂O

9: Et₃N / CH₂Cl₂ / 0 °C

10: pyridine

11: p-TSA / Heating

12: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature

With pyridine; p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tributyltin fluoride; potassium carbonate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium on activated charcoal; bis(tris(4-methyl)phenylphosphine)palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; benzene;

DOI:10.1021/jo990469g

Reference yield:

(3S,4S)-3-Azido-1-(2-bromo-phenyl)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine (239103-16-3) → Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester (239103-26-5)

Guidance literature:

Multi-step reaction with 11 steps

1: Bu₃SnF / Pd(Tol₃P)2Cl₂ / benzene / Heating

2: H₂ / Pd/C / ethyl acetate

3: Et₃N / CH₂Cl₂

4: TBAF / tetrahydrofuran

5: Et₃N / CH₂Cl₂ / 0 °C

6: DBU / 23 °C

7: K₂CO₃ / methanol; H₂O

8: Et₃N / CH₂Cl₂ / 0 °C

9: pyridine

10: p-TSA / Heating

11: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature

With pyridine; p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tributyltin fluoride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; bis(tris(4-methyl)phenylphosphine)palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/jo990469g

Reference yield:

{2-[3-azido-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidin-1-yl]-phenyl}-acetic acid tert-butyl ester (239103-17-4) → Diazo-{2-[(3aS,6aR)-2-oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester (239103-26-5)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / Pd/C / ethyl acetate

2: Et₃N / CH₂Cl₂

3: TBAF / tetrahydrofuran

4: Et₃N / CH₂Cl₂ / 0 °C

5: DBU / 23 °C

6: K₂CO₃ / methanol; H₂O

7: Et₃N / CH₂Cl₂ / 0 °C

8: pyridine

9: p-TSA / Heating

10: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature

With pyridine; p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo990469g

upstream raw materials:

{2-[(3aS,6aR)-2-Oxo-3-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-d]oxazol-5-yl]-phenyl}-acetic acid methyl ester

1-Bromo-2-iodobenzene

[2-((3S,4R)-3-Amino-4-hydroxy-pyrrolidin-1-yl)-phenyl]-acetic acid tert-butyl ester

[2-(2-trifluoromethyl-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]oxazol-5-yl)-phenyl]-acetic acid tert-butyl ester

Downstream raw materials:

1-hydroxy-2-(toluene-4-sulfonylamino)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxylic acid methyl ester

1-chloro-2-(toluene-4-sulfonylamino)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxylic acid methyl ester

C₂₁H₁₈N₂O₆S

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