methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

Base Information

Chemical Name:methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate
CAS No.:117162-22-8
Molecular Formula:C₃₉H₄₁N₃O₆
Molecular Weight:647.771
Hs Code.:

Synonyms:methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

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Chemical Property of methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

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Technology Process of methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

There total 8 articles about methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate 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: 73.0%

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

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

: 117162-22-8
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; 1.) -23 deg C, 2 h, 2.) RT, overnight;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-22-8
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: Multi-step reaction with 8 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

8: 73 percent / N-methylmorpholine, 1-hydroxybenzotriazole (HOBT), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, overnight

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridinium chlorochromate; In methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-22-8
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: Multi-step reaction with 7 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

7: 73 percent / N-methylmorpholine, 1-hydroxybenzotriazole (HOBT), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, overnight

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridinium chlorochromate; In methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00259a003