Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

Base Information

Chemical Name:Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester
CAS No.:753487-52-4
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

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Chemical Property of Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

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Technology Process of Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

There total 6 articles about Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-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:

: 753487-51-3
Benzoic acid (2R,4S)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-tert-butoxycarbonylamino-2-methyl-5-oxo-pentyl ester

: 753487-52-4
Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

Guidance literature:: Benzoic acid (2R,4S)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-tert-butoxycarbonylamino-2-methyl-5-oxo-pentyl ester; With dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 0.166667h;

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;
DOI:10.1021/ol049065n

Reference yield:

: Benzoic acid (R)-4-chlorocarbonyl-2-methyl-butyl ester

: 753487-52-4
Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 7.21 g / tetrahydrofuran / 4 h / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: trisyl azide / tetrahydrofuran / 0.05 h / -78 °C

2.3: 73 percent / KOAc; HOAc / tetrahydrofuran / 2.5 h / 30 °C

3.1: 85 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

4.1: aq. H₂O₂ / tetrahydrofuran; H₂O / 0.17 h / 0 °C

4.2: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

With hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate;
DOI:10.1021/ol049065n

Reference yield:

: 914641-62-6
Benzoic acid (R)-4-carboxy-2-methyl-butyl ester

: 753487-52-4
Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 2 h / 20 °C

2.1: 7.21 g / tetrahydrofuran / 4 h / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: trisyl azide / tetrahydrofuran / 0.05 h / -78 °C

3.3: 73 percent / KOAc; HOAc / tetrahydrofuran / 2.5 h / 30 °C

4.1: 85 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

5.1: aq. H₂O₂ / tetrahydrofuran; H₂O / 0.17 h / 0 °C

5.2: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

With oxalyl dichloride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;
DOI:10.1021/ol049065n