Technology Process of [(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
There total 10 articles about [(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 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 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
10: 50 mg / TEA / 2 h
With
triethylsilane; dmap; TEA; 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
- Guidance literature:
-
Multi-step reaction with 8 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
8: 50 mg / TEA / 2 h
With
TEA; 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
- Guidance literature:
-
Multi-step reaction with 9 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
6: H2 / 10percent Pd/C / aq. ethanol / 2 h / 2068.65 Torr
7: 56 percent / HATU; diisopropylethylamine / dimethylformamide / 4 h / 20 °C
8: iodobenzene bis(trifluoroacetate) / tetrahydrofuran; H2O / 20 °C
9: 50 mg / TEA / 2 h
With
triethylsilane; TEA; 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; acetone; acetonitrile;
8: Hofmann rearrangement;
DOI:10.1021/jo011041w