(S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine

Base Information

• Chemical Name: (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine
• CAS No.: 199853-70-8
• Molecular Formula: C₂₀H₂₁F₃N₂O₃S
• Molecular Weight: 426.46

Synonyms:(S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine

Chemical Property of (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine

Chemical Property:

Purity/Quality:

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Technology Process of (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine

There total 11 articles about (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine 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: 73.0%

(S)-3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propanol (199853-69-5) → (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine (199853-70-8)

Guidance literature:

With bromine; triethylamine; triphenylphosphine; In acetonitrile; for 3.5h; Ambient temperature;

DOI:10.1002/jhet.5570340516

Reference yield:

2-(S)-p-toluenesulfonylamino-β-alanine (21753-19-5) → (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine (199853-70-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / aq. NaOH / dioxane / 3 h / Ambient temperature

2: 99 percent / NaHCO₃ / dimethylformamide / 18 h / Ambient temperature

3: 89 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 18 h / Ambient temperature

4: CF₃COOH / 1 h / Ambient temperature

5: NaHCO₃ / methanol / 4.5 h / Heating

6: NaBH₄ / tetrahydrofuran / 4 h / Ambient temperature

7: 97 percent / Et₃N / CHCl₃ / a) 5 deg C, 1 h, b) RT, 2 h

8: 73 percent / Br₂, PPh₃, Et₃N / acetonitrile / 3.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; bromine; sodium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jhet.5570340516

Reference yield:

N2-(toluene-4-sulfonyl)-L-asparagine (36212-66-5) → (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine (199853-70-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 78 percent / Br₂, aq. NaOH / 0.25 h / 80 °C

2: 96 percent / aq. NaOH / dioxane / 3 h / Ambient temperature

3: 99 percent / NaHCO₃ / dimethylformamide / 18 h / Ambient temperature

4: 89 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 18 h / Ambient temperature

5: CF₃COOH / 1 h / Ambient temperature

6: NaHCO₃ / methanol / 4.5 h / Heating

7: NaBH₄ / tetrahydrofuran / 4 h / Ambient temperature

8: 97 percent / Et₃N / CHCl₃ / a) 5 deg C, 1 h, b) RT, 2 h

9: 73 percent / Br₂, PPh₃, Et₃N / acetonitrile / 3.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; bromine; sodium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jhet.5570340516

upstream raw materials:

(S)-3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propanol

2-(S)-p-toluenesulfonylamino-β-alanine

N²-(toluene-4-sulfonyl)-L-asparagine

N^α-Tosyl-N^β-(tert-butpxycarbonyl)-L-α,β-diamonopropionic acid

Downstream raw materials:

(R)-6-amino-1-methyl-4-(3-methylbenzyl)hexahydro-1,4-diazepine

(S)-N-methyl-N-[3-(3-methylbenzyl)-amino-2-(4-toluenesulfonyl)amino-1-propyl]aminoacetic acid

4-Methyl-N-[(R)-4-methyl-1-(3-methyl-benzyl)-2-oxo-[1,4]diazepan-6-yl]-benzenesulfonamide

4-Methyl-N-[(R)-1-methyl-4-(3-methyl-benzyl)-[1,4]diazepan-6-yl]-benzenesulfonamide

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