5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

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Chemical Name:5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide
CAS No.:189218-06-2
Molecular Formula:C₃₇H₄₉FN₂O₃
Molecular Weight:588.806
Hs Code.:

Synonyms:5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

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Chemical Property of 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

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Technology Process of 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

There total 10 articles about 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] 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: 74.0%

: (S)-2-amino-3,3,N-trimethylbutyramide hydrochloride

: 189218-03-9
5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid

: 189218-06-2
5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

Guidance literature:: With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

: 142-61-0
Hexanoyl chloride

: 189218-06-2
5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / n-butyllithium / pentane; tetrahydrofuran / -78 - 0 °C

2.1: titanium(IV) chloride; triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.2: 90 percent / CH₂Cl₂ / 5 h / 0 - 20 °C

3.1: 96 percent / hydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

4.1: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

5.1: 74 percent / N-iodosuccinimide; triphenylphosphine / dimethylformamide / 2 h / 0 - 20 °C

6.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

6.2: 62 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

7.1: 57 percent / aq. HCl / tetrahydrofuran / 48 h / Heating

8.1: 74 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate; N-methylmorpholine / dimethylformamide / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; titanium tetrachloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; pentane; 1.1: Acylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: Condensation;
DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

: 143965-32-6
(4S)-3-hexanoyl-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 189218-06-2
5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine methylamide] amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: titanium(IV) chloride; triethylamine / CH₂Cl₂ / 1 h / 0 °C

1.2: 90 percent / CH₂Cl₂ / 5 h / 0 - 20 °C

2.1: 96 percent / hydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

3.1: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

4.1: 74 percent / N-iodosuccinimide; triphenylphosphine / dimethylformamide / 2 h / 0 - 20 °C

5.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

5.2: 62 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

6.1: 57 percent / aq. HCl / tetrahydrofuran / 48 h / Heating

7.1: 74 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate; N-methylmorpholine / dimethylformamide / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; dihydrogen peroxide; titanium tetrachloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Substitution / 5.1: Metallation / 5.2: Alkylation / 6.1: Hydrolysis / 7.1: Condensation;
DOI:10.1016/S0040-4020(99)00334-8