[(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

Base Information

Chemical Name:[(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
CAS No.:446880-50-8
Molecular Formula:C₂₉H₄₂N₄O₇
Molecular Weight:558.675
Hs Code.:

Synonyms:[(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

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Chemical Property of [(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

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Technology Process of [(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

There total 9 articles about [(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 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:

: 330187-64-9
[(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

: 446880-50-8
[(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

Guidance literature:: With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1021/jo011041w

Reference yield:

: 141743-16-0
N-(carboxymethyl)-N-Fmoc-glycine tert-butyl ester

: 446880-50-8
[(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

Guidance literature:: Multi-step reaction with 9 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

9: iodobenzene bis(trifluoroacetate) / tetrahydrofuran; H₂O / 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; bis-[(trifluoroacetoxy)iodo]benzene; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 9: Hofmann rearrangement;
DOI:10.1021/jo011041w

Reference yield:

: 330187-55-8
(9H-Fluoren-9-yl)methyl(tert-butoxycarbonyl)methylformylmethyl carbamate

: 446880-50-8
[(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

Guidance literature:: Multi-step reaction with 7 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

7: iodobenzene bis(trifluoroacetate) / tetrahydrofuran; H₂O / 20 °C

With hydrogen; sodium tris(acetoxy)borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; bis-[(trifluoroacetoxy)iodo]benzene; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 10percent Pd/C; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile; 7: Hofmann rearrangement;
DOI:10.1021/jo011041w