((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid

Base Information

• Chemical Name: ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid
• CAS No.: 653587-60-1
• Molecular Formula: C₃₉H₄₅F₃N₆O₈
• Molecular Weight: 782.817
• Mol file: 653587-60-1.mol

Synonyms:

Chemical Property of ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid

There total 9 articles about ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic 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:

((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid tert-butyl ester → ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid (653587-60-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h;

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]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid (653587-60-1)

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

Reference yield:

2-benzyl-2-benzyloxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester → ((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid (653587-60-1)

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-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide

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

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

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

Downstream raw materials:

[3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester