(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

Base Information

Chemical Name:(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate
CAS No.:117162-24-0
Molecular Formula:C₃₆H₄₃N₃O₆
Molecular Weight:613.754
Hs Code.:

(2S)-methyl 2-<3-<<N-(tert-butyloxycarbonyl)-L-phenylalaninyl>amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

Synonyms:(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

Chemical Property:

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Technology Process of (2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

There total 7 articles about (2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate 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: 80.0%

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 117162-20-6
2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

: 117162-24-0
(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

Guidance literature:: With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; 1.) 0 deg C, 2 h, 2.) RT, overnight;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-24-0
(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

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: 84 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3.5 h / 735.5 Torr / Ambient temperature

8: 80 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), Et₃N / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) RT, overnight

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; hydrogen; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-24-0
(2S)-methyl 2-<3-<amino>-3-(phenylmethyl)-2-oxo-1-piperidinyl>-3-phenylpropionate

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: 84 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3.5 h / 735.5 Torr / Ambient temperature

7: 80 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), Et₃N / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) RT, overnight

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; hydrogen; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo00259a003