Technology Process of [2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester
There total 13 articles about [2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(S)-3-(4-benzyloxy-3-acetamido-2-nitrophenyl)-2-[(methoxycarbonyl)amino]-1-propanol;
With
potassium hydroxide;
In
methanol;
at 50 ℃;
di-tert-butyl dicarbonate;
With
sodium hydrogencarbonate;
for 32h;
DOI:10.1021/jo990605h
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 100 percent / NaOH; NaHCO3 / H2O; CHCl3 / 2 h
2.1: 85 percent / La(NO3)2*6H2O; NaNO3; 6N HCl / CH2Cl2 / 6 h / 0 - 20 °C
3.1: H2 / Pd/C / ethyl acetate / 22800 Torr
4.1: 80 percent / Et3N / CH2Cl2 / 2 h / -10 °C
5.1: LiBH4 / tetrahydrofuran / 5 h / 20 °C
6.1: 78 percent / pyridine / 8 h / 20 °C
7.1: 40 percent / HNO3 / acetic anhydride / -13 °C
8.1: Na2CO3 / methanol; H2O / 2 h
9.1: 79 percent / K2CO3 / dimethylformamide / 3 h / 50 °C
10.1: 10 percent KOH / methanol / 50 °C
10.2: 44 percent / NaHCO3 / 32 h
With
hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; lithium borohydride; lanthanum nitrate; hydrogen; nitric acid; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic anhydride; ethyl acetate; N,N-dimethyl-formamide;
1.1: NH2-protection / 2.1: Nitration / 3.1: Reduction / 4.1: Acetylation / 5.1: Reduction / 6.1: Acetylation / 7.1: Nitration / 8.1: Deacetylation / 9.1: Substitution / 10.1: Hydrolysis / 10.2: NH2-protection;
DOI:10.1021/jo990605h
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: SOCl2 / Heating
2.1: 100 percent / NaOH; NaHCO3 / H2O; CHCl3 / 2 h
3.1: 85 percent / La(NO3)2*6H2O; NaNO3; 6N HCl / CH2Cl2 / 6 h / 0 - 20 °C
4.1: H2 / Pd/C / ethyl acetate / 22800 Torr
5.1: 80 percent / Et3N / CH2Cl2 / 2 h / -10 °C
6.1: LiBH4 / tetrahydrofuran / 5 h / 20 °C
7.1: 78 percent / pyridine / 8 h / 20 °C
8.1: 40 percent / HNO3 / acetic anhydride / -13 °C
9.1: Na2CO3 / methanol; H2O / 2 h
10.1: 79 percent / K2CO3 / dimethylformamide / 3 h / 50 °C
11.1: 10 percent KOH / methanol / 50 °C
11.2: 44 percent / NaHCO3 / 32 h
With
hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; lithium borohydride; thionyl chloride; lanthanum nitrate; hydrogen; nitric acid; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic anhydride; ethyl acetate; N,N-dimethyl-formamide;
1.1: Esterification / 2.1: NH2-protection / 3.1: Nitration / 4.1: Reduction / 5.1: Acetylation / 6.1: Reduction / 7.1: Acetylation / 8.1: Nitration / 9.1: Deacetylation / 10.1: Substitution / 11.1: Hydrolysis / 11.2: NH2-protection;
DOI:10.1021/jo990605h
