(R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid

Base Information

• Chemical Name: (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid
• CAS No.: 1357576-21-6
• Molecular Formula: C₃₄H₄₃ClNO₇P
• Molecular Weight: 644.145

Synonyms:(R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid

Chemical Property of (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid

There total 11 articles about (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid 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: 25.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid (1357575-28-0) + di-tert-butyl phosphate silver salt (18281-42-0) → (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid (1357576-21-6)

Guidance literature:

formaldehyd; (R)-4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid; With hydrogenchloride; In toluene; at 0 ℃; for 1h;

di-tert-butyl phosphate silver salt; In toluene; for 0.25h;

Reference yield:

4-Chlorophenylboronic acid (1679-18-1) → (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid (1357576-21-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / Inert atmosphere; Reflux

2.1: TurboGrignard / tetrahydrofuran / -15 - 25 °C / Inert atmosphere

2.2: 1.58 h / 0 °C

3.1: trifluoroacetic acid / dichloromethane; methanol / 0.67 h / 18 - 25 °C

4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 h / 120 °C

4.2: 24 h / 120 °C

5.1: Chiralpak IA column / isopropyl alcohol / Resolution of racemate

6.1: water / tetrahydrofuran; methanol / 50 °C

6.2: pH ~ 5

7.1: hydrogenchloride / toluene / 1 h / 0 °C

7.2: 0.25 h

With hydrogenchloride; TurboGrignard; water; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; toluene; 1.1: Suzuki Coupling;

Reference yield:

2,3-dibromobenzene (583-53-9) → (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid (1357576-21-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / Inert atmosphere; Reflux

2.1: TurboGrignard / tetrahydrofuran / -15 - 25 °C / Inert atmosphere

2.2: 1.58 h / 0 °C

3.1: trifluoroacetic acid / dichloromethane; methanol / 0.67 h / 18 - 25 °C

4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 h / 120 °C

4.2: 24 h / 120 °C

5.1: Chiralpak IA column / isopropyl alcohol / Resolution of racemate

6.1: water / tetrahydrofuran; methanol / 50 °C

6.2: pH ~ 5

7.1: hydrogenchloride / toluene / 1 h / 0 °C

7.2: 0.25 h

With hydrogenchloride; TurboGrignard; water; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; toluene; 1.1: Suzuki Coupling;

upstream raw materials:

2-bromo-4,4’-dichloro-1,1’-biphenyl

4-Chlorophenylboronic acid

formaldehyd

(R)-4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid

Downstream raw materials:

di-tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)-phenyl)piperidin-4-yl)methoxy)methyl phosphate

tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methoxy)methyl hydrogen phosphate

di-tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-((S)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methoxy)methyl phosphate

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