(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

Base Information

Chemical Name:(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide
CAS No.:885021-57-8
Molecular Formula:C₂₉H₄₅N₃O₃
Molecular Weight:483.695
Hs Code.:

Synonyms:(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

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Technology Process of (Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

There total 9 articles about (Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide 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:

: 103882-09-3,62129-44-6
N-Boc-4-I-Phe-OH

: 885021-57-8
(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

Guidance literature:: Multi-step reaction with 9 steps

1.1: isobutyl chloroformate; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

1.2: 89 percent / aq. NaBH₄ / tetrahydrofuran / 0.5 h / -15 °C

2.1: 54 percent / Pd(OAc)2; PPh₃; Et₃N / dimethylformamide / 12 h / 80 °C

3.1: HCl / ethyl acetate / 5 h / 20 °C

4.1: HOBt; EDC / dimethylformamide / 1.25 h / 0 - 20 °C

4.2: 944 mg / Et₃N / dimethylformamide / 12 h / 20 °C

5.1: aq. LiOH / tetrahydrofuran / 18 h / 50 °C

6.1: 363 mg / pyridine / 4 h / 20 °C

7.1: oxalyl dichloride; DMF / CH₂Cl₂ / 1 h / 0 °C

8.1: Et₃N / dimethylformamide; diethyl ether / 5 h / 0 °C

9.1: 24 mg / aq. LiOH / tetrahydrofuran / 3.5 h / 0 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; palladium diacetate; lithium hydroxide; oxalyl dichloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm051226l

Reference yield:

: 885022-46-8
Acetic acid (S)-3-[4-(2-diazo-acetyl)-phenyl]-2-((Z)-octadec-9-enoylamino)-propyl ester

: 885021-57-8
(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 3.5h;
DOI:10.1021/jm051226l

Reference yield:

: 885022-30-0
(S)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol

: 885021-57-8
(Z)-Octadec-9-enoic acid {(S)-2-[4-(2-diazo-acetyl)-phenyl]-1-hydroxymethyl-ethyl}-amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: HCl / ethyl acetate / 5 h / 20 °C

2.1: HOBt; EDC / dimethylformamide / 1.25 h / 0 - 20 °C

2.2: 944 mg / Et₃N / dimethylformamide / 12 h / 20 °C

3.1: aq. LiOH / tetrahydrofuran / 18 h / 50 °C

4.1: 363 mg / pyridine / 4 h / 20 °C

5.1: oxalyl dichloride; DMF / CH₂Cl₂ / 1 h / 0 °C

6.1: Et₃N / dimethylformamide; diethyl ether / 5 h / 0 °C

7.1: 24 mg / aq. LiOH / tetrahydrofuran / 3.5 h / 0 °C

With pyridine; hydrogenchloride; lithium hydroxide; oxalyl dichloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm051226l