N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

Base Information

Chemical Name:N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide
CAS No.:247197-44-0
Molecular Formula:C₂₃H₂₉N₃O₄
Molecular Weight:411.501
Hs Code.:

<i>N</i>-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[<i>e</i>][1,4]diazocin-8-yl)-acetamide

Synonyms:N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

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Chemical Property of N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

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Technology Process of N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

There total 15 articles about N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide 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: 63.0%

: 247197-42-8
(2S)-N-[5-benzoxy-4-acetamido-(S)-2-[2-(tert-butoxycarbonyl)amino-3-acetoxypropyl]phenyl]valine methyl ester

: 247197-44-0
N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

Guidance literature:: (2S)-N-[5-benzoxy-4-acetamido-(S)-2-[2-(tert-butoxycarbonyl)amino-3-acetoxypropyl]phenyl]valine methyl ester; With sodium hydroxide; In methanol; water;

With trifluoroacetic acid; In dichloromethane; at -10 ℃; for 1h;

With diphenyl-phosphinic acid; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 18h;
DOI:10.1021/jo990605h

Reference yield:

: 1080-06-4
L-Tyr-OMe

: 247197-44-0
N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 100 percent / NaOH; NaHCO₃ / H₂O; CHCl₃ / 2 h

2.1: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 22800 Torr

4.1: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

5.1: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

6.1: 78 percent / pyridine / 8 h / 20 °C

7.1: 36 percent / HNO₃ / acetic anhydride / -13 °C

8.1: Na₂CO₃ / methanol; H₂O / 2 h

9.1: 81 percent / K₂CO₃ / dimethylformamide / 3 h / 50 °C

10.1: 10 percent KOH / methanol / 50 °C

10.2: 81 percent / NaHCO₃ / 32 h

11.1: 90 percent / pyridine / 0.17 h / 50 °C

12.1: SnCl₂ / ethanol / 1 h / Heating

13.1: 81 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

14.1: NaOH / H₂O; methanol

14.2: TFA / CH₂Cl₂ / 1 h / -10 °C

14.3: 63 percent / DPPA; Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; lithium borohydride; lanthanum nitrate; hydrogen; nitric acid; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; water; acetic anhydride; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: NH2-protection / 2.1: Nitration / 3.1: Reduction / 4.1: Acetylation / 5.1: Reduction / 6.1: Acetylation / 7.1: Nitration / 8.1: Deacetylation / 9.1: Substitution / 10.1: Hydrolysis / 10.2: NH2-protection / 11.1: Acetylation / 12.1: Reduction / 13.1: Substitution / 14.1: Hydrolysis / 14.2: NH2-deprotection / 14.3: Cyclization;
DOI:10.1021/jo990605h

Reference yield:

: 215300-34-8
(S)-3-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino]-1-propanoic acid methyl ester

: 247197-44-0
N-(9-benzyloxy-5-hydroxymethyl-2-isopropyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-8-yl)-acetamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

2.1: H₂ / Pd/C / ethyl acetate / 22800 Torr

3.1: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

4.1: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

5.1: 78 percent / pyridine / 8 h / 20 °C

6.1: 36 percent / HNO₃ / acetic anhydride / -13 °C

7.1: Na₂CO₃ / methanol; H₂O / 2 h

8.1: 81 percent / K₂CO₃ / dimethylformamide / 3 h / 50 °C

9.1: 10 percent KOH / methanol / 50 °C

9.2: 81 percent / NaHCO₃ / 32 h

10.1: 90 percent / pyridine / 0.17 h / 50 °C

11.1: SnCl₂ / ethanol / 1 h / Heating

12.1: 81 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

13.1: NaOH / H₂O; methanol

13.2: TFA / CH₂Cl₂ / 1 h / -10 °C

13.3: 63 percent / DPPA; Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; lithium borohydride; lanthanum nitrate; hydrogen; nitric acid; sodium carbonate; potassium carbonate; triethylamine; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic anhydride; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Nitration / 2.1: Reduction / 3.1: Acetylation / 4.1: Reduction / 5.1: Acetylation / 6.1: Nitration / 7.1: Deacetylation / 8.1: Substitution / 9.1: Hydrolysis / 9.2: NH2-protection / 10.1: Acetylation / 11.1: Reduction / 12.1: Substitution / 13.1: Hydrolysis / 13.2: NH2-deprotection / 13.3: Cyclization;
DOI:10.1021/jo990605h