(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide

Base Information

• Chemical Name: (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide
• CAS No.: 653587-69-0
• Molecular Formula: C₁₇H₁₂BrNO₃
• Molecular Weight: 358.191
• Mol file: 653587-69-0.mol

Synonyms:

Chemical Property of (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide

There total 1 articles about (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide 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:

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid (3588-64-5,5123-55-7,32150-90-6,38229-08-2) → (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide (653587-69-0)

Guidance literature:

With 1-bromo-N,N,2-trimethyl-1-propen-1-amine; In dichloromethane; for 0.166667h;

DOI:10.1021/jm0511334

Reference yield:

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide (653587-69-0) → 2-[(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3-methyl-2-trifluoromethyl-butyric acid

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 3 h / 0 - 20 °C

2: BBr₃ / CH₂Cl₂ / 4 h / Heating

With boron tribromide; In dichloromethane;

DOI:10.1021/jm0511334

Reference yield:

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide (653587-69-0) → ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-3-methyl-2-trifluoromethyl-butyrylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid (881853-84-5)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 3 h / 0 - 20 °C

2: BBr₃ / CH₂Cl₂ / 4 h / Heating

3: HATU; DIEA / acetonitrile / 1 h

4: NH₂NH₂*H₂O / ethanol / 1.5 h / Heating

5: HOBT; TBTU; DIEA / acetonitrile / 1 h

6: piperidine / CH₂Cl₂ / 2 h / 20 °C

7: TFA / CH₂Cl₂ / 1 h

With piperidine; boron tribromide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm0511334

upstream raw materials:

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid

Downstream raw materials:

2-[(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3-methyl-2-trifluoromethyl-butyric acid ethyl ester

2-Benzyl-2-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3,3,3-trifluoro-propionic acid ethyl ester

2-Benzyl-2-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3,3,3-trifluoro-propionic acid

{(S)-2-[2-((R)-2-Amino-3-phenyl-propionylamino)-2-benzyl-3,3,3-trifluoro-propionylamino]-5-benzyloxycarbonylamino-pentanoylamino}-acetic acid tert-butyl ester