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

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester
• CAS No.: 204329-88-4
• Molecular Formula: C₂₂H₃₀F₃N₃O₄
• Molecular Weight: 457.493

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

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

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 tert-butyl ester

There total 16 articles about (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester 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: 71.0%

2-tert-butyl-1,3-diisopropylisourea (71432-55-8) + (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid (204329-87-3) → (S)-2-tert-Butoxycarbonylamino-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester (204329-88-4)

Guidance literature:

In dichloromethane; Heating;

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 tert-butyl ester (204329-88-4)

Guidance literature:

Multi-step reaction with 14 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

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; dichloromethane; 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 tert-butyl ester (204329-88-4)

Guidance literature:

Multi-step reaction with 15 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

15: 71 percent / CH₂Cl₂ / Heating

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; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1998.203

upstream raw materials:

2-tert-butyl-1,3-diisopropylisourea

(S)-2-tert-Butoxycarbonylamino-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-[(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

(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

(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

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