D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-

Base Information

• Chemical Name: D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-
• CAS No.: 173775-54-7
• Molecular Formula: C14H17FN2O6
• Molecular Weight: 328.297
• DSSTox Substance ID: DTXSID80455973
• Nikkaji Number: J1.360.165H
• Wikidata: Q82278153
• Mol file: 173775-54-7.mol

Synonyms:D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-;173775-54-7;DTXSID80455973;N-boc-4-fluoro-3-nitro-d-phenylalanine;N-(tert-Butoxycarbonyl)-3-nitro-4-fluoro-D-phenylalanine

Chemical Property of D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 328.10706443
• Heavy Atom Count: 23
• Complexity: 459

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=C(C=C1)F)[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC(=C(C=C1)F)[N+](=O)[O-])C(=O)O

Technology Process of D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-

There total 16 articles about D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro- 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: 100.0%

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine methyl ester (331731-26-1) → (R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine (173775-54-7)

Guidance literature:

With lithium hydroxide; In water; tert-butyl alcohol; at 0 ℃; for 0.5h;

DOI:10.1021/ja003835i

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → (R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine (173775-54-7)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / methanol

2: PBr₃ / diethyl ether

3: 80 percent / N-benzylcinchoninium bromide, 50 percent aq. NaOH

4: methanolic HCl

5: SOCl₂

6: NaHCO₃ / tetrahydrofuran

7: K₂CO₃ / methanol; H₂O

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; N-benzylcinchoninium bromide; phosphorus tribromide; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1016/0040-4039(96)00459-5

Reference yield:

4-(bromomethyl)-1-fluoro-2-nitrobenzene (15017-52-4) → (R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine (173775-54-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / n-BuLi; CuCN

2: 87 percent / TFA

3: 82 percent / NaHCO₃ / CH₂Cl₂ / 16 h / 25 °C

4: 100 percent / LiOH*H₂O / H₂O; 2-methyl-propan-2-ol / 0.5 h / 0 °C

With lithium hydroxide; n-butyllithium; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; water; tert-butyl alcohol; 1: Schollkopf alkylation;

DOI:10.1021/ja003835i

upstream raw materials:

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine methyl ester

di-tert-butyl dicarbonate

4-(bromomethyl)-1-fluoro-2-nitrobenzene

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

Downstream raw materials:

methyl N-[N-(tert-butyloxycarbonyl)-L-(3,4-dihydroxyphenylalanyl)]-D-4-fluoro-3-nitrophenylalaninate

C₄₅H₄₉F₂N₇O₁₆

(S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-propionic acid

[(8R,11S,14R)-8-Hydroxymethyl-11-(3-isopropoxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaen-14-yl]-carbamic acid tert-butyl ester