[(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

Base Information

• Chemical Name: [(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
• CAS No.: 330187-64-9
• Molecular Formula: C₃₀H₄₂N₄O₈
• Molecular Weight: 586.685

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

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Technology Process of [(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

There total 9 articles about [(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 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: 56.0%

3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester (446880-45-1) → [(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 (330187-64-9)

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

Reference yield:

(S)-2-amino-3-phenylpropionamide hydrochloride (65864-22-4) → [(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 (330187-64-9)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: DBU / acetonitrile / 0.5 h / 20 °C

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

5: H₂ / 10percent Pd/C / aq. ethanol / 2 h / 2068.65 Torr

6: 56 percent / HATU; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With hydrogen; 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 ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo011041w

Reference yield:

N-(carboxymethyl)-N-Fmoc-glycine tert-butyl ester (141743-16-0) → [(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 (330187-64-9)

Guidance literature:

Multi-step reaction with 8 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

7: H₂ / 10percent Pd/C / aq. ethanol / 2 h / 2068.65 Torr

8: 56 percent / HATU; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With triethylsilane; dmap; hydrogen; 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 ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo011041w

upstream raw materials:

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

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

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