Technology Process of N--L-leucyl>-L-prolyl>-N-methyl-L-phenylalanine ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)
There total 7 articles about N--L-leucyl>-L-prolyl>-N-methyl-L-phenylalanine ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl) which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 94 percent / KOH, nBu4NHSO4 / tetrahydrofuran / 0.5 h / Ambient temperature
2: 64 percent / Et3N, DMAP, isopropenyl chloroformate / CH2Cl2 / 1 h / 0 °C
3: 93 percent / H2 / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr
4: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH2Cl2, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h
5: MgBr2*Et2O / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h
6: 1.) NMM, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.) 0 deg C, 1 h; room temperature, 3 h
With
4-methyl-morpholine; dmap; potassium hydroxide; Isopropenyl chloroformate; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 64 percent / Et3N, DMAP, isopropenyl chloroformate / CH2Cl2 / 1 h / 0 °C
2: 93 percent / H2 / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr
3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH2Cl2, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h
4: MgBr2*Et2O / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h
5: 1.) NMM, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.) 0 deg C, 1 h; room temperature, 3 h
With
4-methyl-morpholine; dmap; Isopropenyl chloroformate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 64 percent / Et3N, DMAP, isopropenyl chloroformate / CH2Cl2 / 1 h / 0 °C
2: 93 percent / H2 / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr
3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH2Cl2, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h
4: MgBr2*Et2O / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h
5: 1.) NMM, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.) 0 deg C, 1 h; room temperature, 3 h
With
4-methyl-morpholine; dmap; Isopropenyl chloroformate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4
