(S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid

Base Information

• Chemical Name: (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid
• CAS No.: 138605-21-7
• Molecular Formula: C₁₇H₂₂N₄O₃
• Molecular Weight: 330.387

Synonyms:(S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid

Chemical Property of (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid

There total 13 articles about (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic 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:

3-phenylglutaric acid anhydride (4160-80-9) → (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid (138605-21-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

2: 100 percent / 2.5 M aq. NaOH

3: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

4: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

5: TsOH / benzene / 2 h / 120 °C

6: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

7: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

8: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

9: 67 percent / acetic acid / tetrahydrofuran; H₂O / 6 h / Heating

10: 1.) 3A molecular sieves, 2.) NaCNBH₄ / 1.) MeOH, 0.5 h, 2.) MeOH, THF, RT, 3 h

11: 84 percent / dimethylformamide / 5 h / 110 °C

12: 32 mg / sat. HCl/EtOAc / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; ethyl acetate; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00083a006

Reference yield:

4-phenyltetrahydropyran-2-one (61198-49-0,61949-75-5,71302-21-1,25547-53-9) → (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid (138605-21-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / 2.5 M aq. NaOH

2: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

3: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

4: TsOH / benzene / 2 h / 120 °C

5: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

6: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

7: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

8: 67 percent / acetic acid / tetrahydrofuran; H₂O / 6 h / Heating

9: 1.) 3A molecular sieves, 2.) NaCNBH₄ / 1.) MeOH, 0.5 h, 2.) MeOH, THF, RT, 3 h

10: 84 percent / dimethylformamide / 5 h / 110 °C

11: 32 mg / sat. HCl/EtOAc / Ambient temperature

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; ethyl acetate; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00083a006

Reference yield:

3-phenylglutaric acid (4165-96-2) → (S)-2-((3S,4R)-3-Azido-2-oxo-4-phenyl-piperidin-1-yl)-hexanoic acid (138605-21-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

2: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

3: 100 percent / 2.5 M aq. NaOH

4: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

5: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

6: TsOH / benzene / 2 h / 120 °C

7: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

8: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

9: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

10: 67 percent / acetic acid / tetrahydrofuran; H₂O / 6 h / Heating

11: 1.) 3A molecular sieves, 2.) NaCNBH₄ / 1.) MeOH, 0.5 h, 2.) MeOH, THF, RT, 3 h

12: 84 percent / dimethylformamide / 5 h / 110 °C

13: 32 mg / sat. HCl/EtOAc / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; ethyl acetate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00083a006

upstream raw materials:

3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

4-phenyltetrahydropyran-2-one

3-phenylglutaric acid anhydride

3-phenylglutaric acid

Downstream raw materials:

3(S)-(acetylamino)-α(S)-butyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-2-oxo-4(R)-phenyl-1-piperidineacetamide

3(S)-<(tert-butyloxycarbonyl)amino>-α(S)-butyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-2-oxo-4(R)-phenyl-1-piperidineacetamide

3(S)-amino-α(S)-butyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-2-oxo-4(R)-phenyl-1-piperidineacetamide

3(S)-azido-α(S)-butyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-2-oxo-4(R)-phenyl-1-piperidineacetamide

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