diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

Base Information

• Chemical Name: diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate
• CAS No.: 643014-13-5
• Molecular Formula: C₄₂H₅₉N₅O₈
• Molecular Weight: 761.959
• Mol file: 643014-13-5.mol

Synonyms:diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

Chemical Property of diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

There total 18 articles about diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 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: 88.0%

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate (643014-12-4) → diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate (643014-13-5)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2004.09.037

Reference yield:

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (88668-76-2) → diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate (643014-13-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: hydrobromic acid; CHCl₃ / 20 °C

2.1: 80 percent / LiBr / acetone / 79 h / 20 °C

3.1: acetonitrile / 46 h / 20 °C

3.2: 91 percent / PPh₃; Et₃N / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

4.1: 56 percent / H₂; trifluoroacetic acid / Pd-C / methanol / 50 h / 3102.89 Torr

5.1: 29 percent / tBuMgCl / diethyl ether / 2 h / 0 °C

6.1: 86 percent / K₂CO₃ / methanol; H₂O / 2 h / Heating

7.1: 80 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

8.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C

9.1: 64 percent / CH₂Cl₂ / 20 °C

10.1: 87 percent / piperidine / dimethylformamide / 2.5 h / 20 °C

11.1: 88 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

12.1: 82 percent / piperidine / dimethylformamide / 2 h / 20 °C

13.1: 82 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

14.1: 88 percent / piperidine / dimethylformamide / 2 h / 20 °C

With piperidine; chloroform; tert-butylmagnesium chloride; hydrogen bromide; hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium bromide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 2.1: Finkelstein reaction / 3.1: Eschenmoser olefination / 3.2: Eschenmoser olefination;

DOI:10.1016/j.tet.2004.09.037

Reference yield:

(S)-N-benzyl-5-thioxoproline tert-butyl ester (90741-31-4) → diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate (643014-13-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: acetonitrile / 46 h / 20 °C

1.2: 91 percent / PPh₃; Et₃N / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

2.1: 56 percent / H₂; trifluoroacetic acid / Pd-C / methanol / 50 h / 3102.89 Torr

3.1: 29 percent / tBuMgCl / diethyl ether / 2 h / 0 °C

4.1: 86 percent / K₂CO₃ / methanol; H₂O / 2 h / Heating

5.1: 80 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

6.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C

7.1: 64 percent / CH₂Cl₂ / 20 °C

8.1: 87 percent / piperidine / dimethylformamide / 2.5 h / 20 °C

9.1: 88 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

10.1: 82 percent / piperidine / dimethylformamide / 2 h / 20 °C

11.1: 82 percent / TBTU; diisopropylethylamine / dimethylformamide / 20 °C

12.1: 88 percent / piperidine / dimethylformamide / 2 h / 20 °C

With piperidine; tert-butylmagnesium chloride; hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Eschenmoser olefination / 1.2: Eschenmoser olefination;

DOI:10.1016/j.tet.2004.09.037

upstream raw materials:

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

methyl (2S)-5-chloro-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

methyl (2S)-5-[(2S,5S)-2-tert-butoxycarbonyl-5-pyrrolidinyl]-2-(2,2,2-trifluoroacetamido)-pentanoate

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Downstream raw materials:

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-benzyloxycarbonylaminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate