(S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

Base Information

• Chemical Name: (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid
• CAS No.: 782432-51-3
• Molecular Formula: C₃₀H₃₆F₃N₅O₆Se
• Molecular Weight: 698.601
• Mol file: 782432-51-3.mol

Synonyms:(S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

Chemical Property of (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

There total 22 articles about (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic 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: 96.0%

(S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester (204329-92-0) → (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (782432-51-3)

Guidance literature:

With hydrogenchloride; trifluoroacetic acid; In ethyl acetate;

DOI:10.1246/cl.1998.203

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (782432-51-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / H₂ / 10percent Pd/C / methanol; H₂O

2: 91 percent / DCC, HOBt, NMM / tetrahydrofuran

3: 57 percent / 3M HCl / ethyl acetate; propan-2-ol

4: 93 percent / EDC, HOBt / dimethylformamide

5: 96 percent / TFA, 1M HCl / ethyl acetate

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1246/cl.1998.203

Reference yield:

3-(4-bromophenyl)propanol (25574-11-2) → (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (782432-51-3)

Guidance literature:

Multi-step reaction with 19 steps

1: imidazole / dimethylformamide

2: 79 percent / 1.) n-BuLi / diethyl ether / -42 °C / 1.) -42 -> 0 deg C

3: 91 percent / NH₂OH*HCl, Et₃N / ethanol / Heating

4: 98 percent / pyridine / 0 deg C -> room temp.

5: 98 percent / liq. NH₃ / diethyl ether / -78 -> -33 deg C -> room temp.

6: 1.) t-BuOCl; 2.) Et₃N / 1.) Et₂O, -50 deg C; 2.) Et₂O, -50 deg C -> room temp.

7: CSA / methanol

8: 95 percent / CBr₄, PPh₃ / toluene

9: 75 percent / NaH / dimethylformamide

10: 3M NaOH / ethanol

11: 95 percent / dioxane / 80 °C

12: 26 percent / acylase, CoCl₂ / H₂O / pH = 7.0

13: 97 percent / Et₃N / dioxane; H₂O

14: 71 percent / CH₂Cl₂ / Heating

15: 73 percent / 3M HCl / ethyl acetate; H₂O

16: 91 percent / DCC, HOBt, NMM / tetrahydrofuran

17: 57 percent / 3M HCl / ethyl acetate; propan-2-ol

18: 93 percent / EDC, HOBt / dimethylformamide

19: 96 percent / TFA, 1M HCl / ethyl acetate

With 4-methyl-morpholine; pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; n-butyllithium; acylase; tert-butylhypochlorite; carbon tetrabromide; camphor-10-sulfonic acid; hydroxylamine hydrochloride; ammonia; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1246/cl.1998.203

upstream raw materials:

(S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester

(S)-2-Hydroxy-3-methylbutanoic acid

3-(4-bromophenyl)propanol

methyl 3-(4-bromopehynl)propanoate

Downstream raw materials:

(3S,6S,9S,12S)-12-Isopropyl-3-methyl-6-phenylselanylmethyl-9-{3-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propyl}-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone