(S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid
• CAS No.: 204329-87-3
• Molecular Formula: C₁₈H₂₂F₃N₃O₄
• Molecular Weight: 401.386

Synonyms:(S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

Chemical Property of (S)-2-tert-Butoxycarbonylamino-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-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

There total 15 articles about (S)-2-tert-Butoxycarbonylamino-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (204329-86-2) → (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (204329-87-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; water;

DOI:10.1246/cl.1998.203

Reference yield:

3-(4-bromophenyl)propanol (25574-11-2) → (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (204329-87-3)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; 1H-imidazole; sodium hydroxide; n-butyllithium; acylase; tert-butylhypochlorite; carbon tetrabromide; camphor-10-sulfonic acid; hydroxylamine hydrochloride; ammonia; sodium hydride; triethylamine; triphenylphosphine; In 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1998.203

Reference yield:

methyl 3-(4-bromopehynl)propanoate (75567-84-9) → (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (204329-87-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 94 percent / LiAlH₄ / diethyl ether / Heating

2: imidazole / dimethylformamide

3: 79 percent / 1.) n-BuLi / diethyl ether / -42 °C / 1.) -42 -> 0 deg C

4: 91 percent / NH₂OH*HCl, Et₃N / ethanol / Heating

5: 98 percent / pyridine / 0 deg C -> room temp.

6: 98 percent / liq. NH₃ / diethyl ether / -78 -> -33 deg C -> room temp.

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

8: CSA / methanol

9: 95 percent / CBr₄, PPh₃ / toluene

10: 75 percent / NaH / dimethylformamide

11: 3M NaOH / ethanol

12: 95 percent / dioxane / 80 °C

13: 26 percent / acylase, CoCl₂ / H₂O / pH = 7.0

14: 97 percent / Et₃N / dioxane; H₂O

With pyridine; 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; acylase; tert-butylhypochlorite; carbon tetrabromide; camphor-10-sulfonic acid; hydroxylamine hydrochloride; ammonia; sodium hydride; triethylamine; triphenylphosphine; In 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1998.203

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-Amino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid

3-(4-bromophenyl)propanol

methyl 3-(4-bromopehynl)propanoate

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester

(S)-2-Amino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester

(S)-2-[(S)-2-((S)-2-Amino-propionyloxy)-3-methyl-butyrylamino]-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester

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

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