(S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone

Base Information

• Chemical Name: (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone
• CAS No.: 131918-93-9
• Molecular Formula: C₃₁H₃₂N₆O₇
• Molecular Weight: 600.631

Synonyms:(S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone

Chemical Property of (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone

Chemical Property:

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• Pictogram(s):  
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Technology Process of (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone

There total 11 articles about (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone 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:

5-nitro-o-toluic acid (1975-52-6) → (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexaone (131918-93-9)

Guidance literature:

Multi-step reaction with 12 steps

1: AcCl / Heating

2: N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / 20 h / Heating

3: NaOH, tricaprylmethylammonium chloride / CH₂Cl₂; H₂O / 5 h / Ambient temperature

4: 82 percent / aq. 4 N KOH / methanol / 4 h / Ambient temperature

5: SOCl₂, DMF / 3 h / Ambient temperature

6: Et₃N / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 2 h

7: H₂ / PtO₂ / dimethylformamide; H₂O / 2 h / Ambient temperature

8: dicyclohexylcarbodiimide (DCC) / dimethylformamide; CH₂Cl₂ / 0 - 20 °C

9: 89 percent / H₂NNH₂*H₂O / methanol / 24 h / Ambient temperature

10: 96 percent / 2 M HCl / acetic acid / 0.5 h / Ambient temperature

11: 8 N HCl, isoamylnitrite / dimethylformamide; tetrahydrofuran / 0.5 h / -40 °C

12: iPr₂NEt / dimethylformamide / 24 h / pH 9

With hydrogenchloride; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; thionyl chloride; Perbenzoic acid; hydrogen; Aliquat 336; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90119-8

Reference yield:

methyl 2-methyl-5-nitrobenzoate (77324-87-9) → (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexaone (131918-93-9)

Guidance literature:

Multi-step reaction with 11 steps

1: N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / 20 h / Heating

2: NaOH, tricaprylmethylammonium chloride / CH₂Cl₂; H₂O / 5 h / Ambient temperature

3: 82 percent / aq. 4 N KOH / methanol / 4 h / Ambient temperature

4: SOCl₂, DMF / 3 h / Ambient temperature

5: Et₃N / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 2 h

6: H₂ / PtO₂ / dimethylformamide; H₂O / 2 h / Ambient temperature

7: dicyclohexylcarbodiimide (DCC) / dimethylformamide; CH₂Cl₂ / 0 - 20 °C

8: 89 percent / H₂NNH₂*H₂O / methanol / 24 h / Ambient temperature

9: 96 percent / 2 M HCl / acetic acid / 0.5 h / Ambient temperature

10: 8 N HCl, isoamylnitrite / dimethylformamide; tetrahydrofuran / 0.5 h / -40 °C

11: iPr₂NEt / dimethylformamide / 24 h / pH 9

With hydrogenchloride; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; thionyl chloride; Perbenzoic acid; hydrogen; Aliquat 336; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90119-8

Reference yield:

methyl 2-(bromomethyl)-5-nitrobenzoate (90725-68-1) → (S)-4-Benzyl-20-phenoxymethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexaone (131918-93-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NaOH, tricaprylmethylammonium chloride / CH₂Cl₂; H₂O / 5 h / Ambient temperature

2: 82 percent / aq. 4 N KOH / methanol / 4 h / Ambient temperature

3: SOCl₂, DMF / 3 h / Ambient temperature

4: Et₃N / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 2 h

5: H₂ / PtO₂ / dimethylformamide; H₂O / 2 h / Ambient temperature

6: dicyclohexylcarbodiimide (DCC) / dimethylformamide; CH₂Cl₂ / 0 - 20 °C

7: 89 percent / H₂NNH₂*H₂O / methanol / 24 h / Ambient temperature

8: 96 percent / 2 M HCl / acetic acid / 0.5 h / Ambient temperature

9: 8 N HCl, isoamylnitrite / dimethylformamide; tetrahydrofuran / 0.5 h / -40 °C

10: iPr₂NEt / dimethylformamide / 24 h / pH 9

With hydrogenchloride; potassium hydroxide; sodium hydroxide; thionyl chloride; hydrogen; Aliquat 336; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90119-8

upstream raw materials:

5-nitro-o-toluic acid

methyl 2-methyl-5-nitrobenzoate

methyl 2-(bromomethyl)-5-nitrobenzoate

2-phenoxymethyl-5-nitrobenzoyl chloride

Downstream raw materials:

(S)-4-Benzyl-20-bromomethyl-2,5,8,11,14,17-hexaaza-bicyclo[17.3.1]tricosa-1⁽²³⁾,19,21-triene-3,6,9,12,15,18-hexaone

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