(R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid

Base Information

• Chemical Name: (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid
• CAS No.: 188729-10-4
• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.459

Synonyms:(R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid

Chemical Property of (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid

Chemical Property:

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Technology Process of (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid

There total 6 articles about (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid 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:

(S)-2-amino-N-methyl-2-phenylacetamide (129213-83-8) → (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid (188729-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HOBT, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

2: 90 percent aq. TFA / 1 h

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm970404a

Reference yield:

(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one (161725-13-9) → (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid (188729-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA / tetrahydrofuran; hexane / -78 - 20 °C

2: 1.) aq. H₂O₂, LiOH, 2.) NaNO₂ / 1.) THF, RT, 1.5 h, 2.) THF, 30 min

3: HOBT, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

4: 90 percent aq. TFA / 1 h

With lithium hydroxide; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium diisopropyl amide; sodium nitrite; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm970404a

Reference yield:

(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid (156109-64-7) → (R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid (188729-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HOBT, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

2: 90 percent aq. TFA / 1 h

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm970404a

upstream raw materials:

(R)-3-[((S)-Methylcarbamoyl-phenyl-methyl)-carbamoyl]-6-phenyl-hexanoic acid tert-butyl ester

(S)-2-amino-N-methyl-2-phenylacetamide

(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one

(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid

Downstream raw materials:

N⁴-benzyloxy-N¹-(methylcarbamoyl-phenyl-methyl)-2-(3-phenyl-propyl)-succinamide

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