[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester
CAS No.:247197-23-5
Molecular Formula:C₂₃H₂₉N₃O₇
Molecular Weight:459.499
Hs Code.:

[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid <i>tert</i>-butyl ester

Synonyms:[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

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Chemical Property of [2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

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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. 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: 46.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 247197-19-9
(S)-3-(4-benzyloxy-3-acetamido-2-nitrophenyl)-2-[(methoxycarbonyl)amino]-1-propanol

: 247197-21-3
(S)-3-(4-benzyloxy-3-amino-2-nitrophenyl)-2-[(tert-butoxycarbonyl)amino]-1-propanol

: 247197-23-5
[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

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

Reference yield:

: 1080-06-4
L-Tyr-OMe

: 247197-23-5
[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

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

Reference yield:

: 60-18-4,18875-48-4,25619-78-7,30704-25-7
L-tyrosine

: 247197-23-5
[2-(3-acetylamino-4-benzyloxy-2-nitro-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

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