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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Chemical Name: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
CAS No.:138571-14-9
Molecular Formula:C₃₆H₅₈N₆O₄
Molecular Weight:638.894
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 14 articles about 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 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:

: 4160-80-9
3-phenylglutaric acid anhydride

: 138571-14-9
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

Guidance literature:: Multi-step reaction with 13 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

13: N-hydroxybenzotriazole, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 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; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; ethyl acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00083a006

Reference yield:

: 61198-49-0,61949-75-5,71302-21-1,25547-53-9
4-phenyltetrahydropyran-2-one

: 138571-14-9
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

Guidance literature:: Multi-step reaction with 12 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

12: N-hydroxybenzotriazole, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; ethyl acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00083a006

Reference yield:

: 4165-96-2
3-phenylglutaric acid

: 138571-14-9
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

Guidance literature:: Multi-step reaction with 14 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

14: N-hydroxybenzotriazole, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 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; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; ethyl acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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