2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

Base Information

Chemical Name:2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid
CAS No.:117162-18-2
Molecular Formula:C₂₉H₃₀N₂O₅
Molecular Weight:486.568
Hs Code.:

Synonyms:2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

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Chemical Property of 2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

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Technology Process of 2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

There total 7 articles about 2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid 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%

: 117162-13-7,117162-14-8
(2S)-methyl 2-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

: 117162-18-2
2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

Guidance literature:: With lithium hydroxide; In 1,2-dimethoxyethane; water; at 0 - 20 ℃; for 1h;
DOI:10.1021/jo00259a003

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 117162-18-2
2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / p-TsOH / toluene / Heating

2: 1.) sodium hexamethyldisilyl amide / 1.) THF, toluene. -78 deg C, 0.5 h

3: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, overnight, 2.) 25 deg C, 10 min

4: 80 percent / PCC, molecular sieves 4A / CH₂Cl₂ / 1 h

5: 1.0 g / NaOAc, NaCNBH₃, molecular sieves 4A / methanol / Ambient temperature

6: AcONa, glacial AcOH (pH 6.5 - 7.0) / methanol / 105 °C

7: 95 percent / LiOH*H₂O / 1,2-dimethoxy-ethane; H₂O / 1 h / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene;
DOI:10.1021/jo00259a003

Reference yield:

: 55740-07-3
(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 117162-18-2
2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) sodium hexamethyldisilyl amide / 1.) THF, toluene. -78 deg C, 0.5 h

2: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, overnight, 2.) 25 deg C, 10 min

3: 80 percent / PCC, molecular sieves 4A / CH₂Cl₂ / 1 h

4: 1.0 g / NaOAc, NaCNBH₃, molecular sieves 4A / methanol / Ambient temperature

5: AcONa, glacial AcOH (pH 6.5 - 7.0) / methanol / 105 °C

6: 95 percent / LiOH*H₂O / 1,2-dimethoxy-ethane; H₂O / 1 h / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; acetic acid; pyridinium chlorochromate; In methanol; 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1021/jo00259a003