N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester

Base Information

• Chemical Name: N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester
• CAS No.: 330187-62-7
• Molecular Formula: C₄₅H₅₆N₄O₁₁
• Molecular Weight: 828.96

Synonyms:N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester

Chemical Property of N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester

There total 7 articles about N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester 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:

N-(carboxymethyl)-N-Fmoc-glycine tert-butyl ester (141743-16-0) → N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester (330187-62-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 93 percent / triethylsilane / 10percent Pd/C / acetone / 0.5 h / 10 - 20 °C

3: NaB(OAc)3H / dimethylformamide / 6 h / 20 °C

4: HATU; diisopropylethylamine / dimethylformamide / 2 h / 20 °C

5: DBU / acetonitrile / 0.5 h / 20 °C

6: HATU; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With triethylsilane; dmap; sodium tris(acetoxy)borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 10percent Pd/C; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo011041w

Reference yield:

N-(S-ethyl-thiocarbonylmethyl)-N-Fmoc-glycine tert-butyl ester (330187-54-7) → N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester (330187-62-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / triethylsilane / 10percent Pd/C / acetone / 0.5 h / 10 - 20 °C

2: NaB(OAc)3H / dimethylformamide / 6 h / 20 °C

3: HATU; diisopropylethylamine / dimethylformamide / 2 h / 20 °C

4: DBU / acetonitrile / 0.5 h / 20 °C

5: HATU; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With triethylsilane; sodium tris(acetoxy)borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 10percent Pd/C; In N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo011041w

Reference yield:

β-cyclohexyl N-benzyloxycarbonylaspartate + 2(S)-[N-[2-[N'-(tert-butyloxycarbonylmethyl)]aminoethyl]-N-[(1',3'-dioxo-3'-benzyloxy)propyl]]-2-amino-3-phenylpropionamide (446880-44-0) → N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester (330187-62-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jo011041w

upstream raw materials:

2(S)-[N-[2-[N'-(tert-butyloxycarbonylmethyl)]aminoethyl]-N-[(1',3'-dioxo-3'-benzyloxy)propyl]]-2-amino-3-phenylpropionamide

(S)-2-amino-3-phenylpropionamide hydrochloride

N-(carboxymethyl)-N-Fmoc-glycine tert-butyl ester

(9H-Fluoren-9-yl)methyl(tert-butoxycarbonyl)methylformylmethyl carbamate

Downstream raw materials:

[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethyl)-6-cyclohexyloxycarbonylmethyl-5,8,10-trioxo-[1,4,7]triazecan-4-yl]-acetic acid tert-butyl ester

[(S)-1-((S)-1-Acetylamino-2-phenyl-ethyl)-6-cyclohexyloxycarbonylmethyl-5,8,10-trioxo-[1,4,7]triazecan-4-yl]-acetic acid tert-butyl ester

[(S)-7-((S)-1-Amino-2-phenyl-ethyl)-4-tert-butoxycarbonylmethyl-3,8,10-trioxo-[1,4,7]triazecan-2-yl]-acetic acid cyclohexyl ester

3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester

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