(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

Base Information

Chemical Name:(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate
CAS No.:885022-42-4
Molecular Formula:C₃₀H₄₇NO₅
Molecular Weight:501.707
Hs Code.:

Synonyms:(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

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Chemical Property of (Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

Chemical Property:

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Technology Process of (Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

There total 6 articles about (Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate 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

: 885022-42-4
(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 885022-42-4
(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: (S)-4-(ethoxycarbonyl)phenylalaninol hydrochloride

: 885022-42-4
(Z)-N-{(1S)-2-hydroxy-1-[(4-carboxyphenyl)methyl]ethyl}-9-octadecenamide acetate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 944 mg / Et₃N / dimethylformamide / 12 h / 20 °C

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

3.1: 363 mg / pyridine / 4 h / 20 °C

With pyridine; lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm051226l