N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide

Base Information

• Chemical Name: N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide
• CAS No.: 484685-81-6
• Molecular Formula: C₃₂H₄₃N₃O₄
• Molecular Weight: 533.711

Synonyms:N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide

Chemical Property of N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide

Chemical Property:

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Technology Process of N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide

There total 2 articles about N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide 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: 87.0%

(S)-2-amino-3-(4-cyanophenyl)-N-methylpropanamide hydrochloride + 2-isobutyl-3-(3-phenyl-propyl)-succinic acid 4-tert-butyl ester; compound with tert-butylamine → N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide (484685-81-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at -15 - 20 ℃;

DOI:10.1016/S0968-0896(02)00109-8

Reference yield:

tert-butyl (S)-(3-(4-cyanophenyl)-1-(methylamino)-1-oxopropan-2-yl)carbamate (228260-15-9) → N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide (484685-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / ethyl acetate

2: 87 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / -15 - 20 °C

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

DOI:10.1016/S0968-0896(02)00109-8

Reference yield: 79.0%

N-[4-tert-butyloxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide (484685-81-6) → N-[4-hydroxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide (484685-84-9)

Guidance literature:

With trifluoroacetic acid; at 5 ℃; for 4h;

DOI:10.1016/S0968-0896(02)00109-8

upstream raw materials:

tert-butyl (S)-(3-(4-cyanophenyl)-1-(methylamino)-1-oxopropan-2-yl)carbamate

Downstream raw materials:

N-[4-hydroxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-cyanophenylalanine N-methylamide

N-[4-hydroxy-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-[N,N'-bis(benzyloxycarbonyl)guanidinomethyl]phenylalanine N-methylamide

N-[4-(N-benzyloxyamino)-2(R)-isobutyl-3(S)-phenylpropylsuccinyl]-L-4'-[N,N'-bis(benzyloxycarbonyl)guanidinomethyl]phenylalanine N-methylamide

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