[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

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Chemical Name:[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester
CAS No.:173918-62-2
Molecular Formula:C₂₃H₃₀F₂N₂O₄
Molecular Weight:436.499
Hs Code.:

Synonyms:[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

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Chemical Property of [4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

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Technology Process of [4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

There total 5 articles about [4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-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: 95.0%

: 173918-54-2
N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

: 173918-62-2
[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: With tin(ll) chloride; In ethanol; for 2h; Title compound not separated from byproducts; Heating;
DOI:10.1016/0040-4020(95)00896-G

Reference yield:

: 173918-49-5
(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosinal

: 173918-62-2
[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

2: 57 percent / ammonia gas / diethyl ether / -78 °C

3: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

4: 95 percent / tin(II)chloride / ethanol / 2 h / Heating

With hydrogenchloride; dimethylsulfide borane complex; ammonia; sodium hydrogencarbonate; sodium carbonate; tin(ll) chloride; zinc; In tetrahydrofuran; diethyl ether; ethanol;
DOI:10.1016/0040-4020(95)00896-G

Reference yield:

: (R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosine methyl ester

: 173918-62-2
[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 51 percent / ddisobutylaluminium hydride / diethyl ether; toluene; hexane / 0.17 h / -78 °C

2: 46 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

3: 57 percent / ammonia gas / diethyl ether / -78 °C

4: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

5: 95 percent / tin(II)chloride / ethanol / 2 h / Heating

With hydrogenchloride; dimethylsulfide borane complex; ammonia; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; tin(ll) chloride; zinc; In tetrahydrofuran; diethyl ether; ethanol; hexane; toluene;
DOI:10.1016/0040-4020(95)00896-G