(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

Base Information

• Chemical Name: (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid
• CAS No.: 156017-45-7
• Molecular Formula: C₂₉H₃₀F₂NO₇P
• Molecular Weight: 573.53
• Mol file: 156017-45-7.mol

Synonyms:(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

Chemical Property of (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

There total 20 articles about (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic 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: 89.0%

Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe (156017-44-6) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid (156017-45-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)75835-7

Reference yield:

diethyl (4-iodobenzoyl)phosphonate (156017-40-2) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid (156017-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / DAST / toluene / 2 h / 0 °C

2: 1.) Zn, 2.) (PPh₃)2PdCl₂ / 1.) THF, DMAC, from 65 deg C to 70 deg C, 1 h, 2.) THF, DMAC, from 65 deg C to 70 deg C, 5 h

3: 66 percent / 0.2 N aq. LiOH / tetrahydrofuran / 0.33 h / 0 °C

4: 1.) TFA, 2.) aq. NaHCO₃ / 1.) RT, 1 h, 2.) dioxane, RT, 2.5 h

With bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; sodium hydrogencarbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; toluene;

DOI:10.1080/00304949609355909

Reference yield:

[Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester (156017-41-3) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid (156017-45-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Zn, 2.) (PPh₃)2PdCl₂ / 1.) THF, DMAC, from 65 deg C to 70 deg C, 1 h, 2.) THF, DMAC, from 65 deg C to 70 deg C, 5 h

2: 66 percent / 0.2 N aq. LiOH / tetrahydrofuran / 0.33 h / 0 °C

3: 1.) TFA, 2.) aq. NaHCO₃ / 1.) RT, 1 h, 2.) dioxane, RT, 2.5 h

With bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; sodium hydrogencarbonate; trifluoroacetic acid; zinc; In tetrahydrofuran;

DOI:10.1080/00304949609355909

upstream raw materials:

Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

4-<(diethylphosphono)difluoromethyl>-L-phenylalanine

diethyl (bromodifluoromethyl)phosphonate

Downstream raw materials:

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid

C₃₂H₃₂F₂NO₇P