(S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester

Base Information

• Chemical Name: (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester
• CAS No.: 166169-81-9
• Molecular Formula: C₂₅H₃₀N₂O₅
• Molecular Weight: 438.524
• Mol file: 166169-81-9.mol

Synonyms:(S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester

Chemical Property of (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester

There total 1 articles about (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester 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: 45.0%

(S)-N-carbobenzoxy-tert-butylleucine (62965-10-0) + (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride (78183-55-8) → (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester (166169-81-9)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; a) from 0 deg C to 5 deg C, 2 h, b) 5 deg C, 16 h;

DOI:10.1021/jm950642a

Reference yield: 100.0%

(S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester (166169-81-9) → (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acid (166169-82-0)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm950642a

Reference yield:

(S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acetic acid, methyl ester (166169-81-9) → (S)-2-({(S)-2-[(S)-2-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propylamino)-3,3-dimethyl-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-methoxy-butyric acid tert-butyl ester (1027306-43-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / 1 N NaOH / methanol / 2 h / Ambient temperature

2: N,N-diisopropylethylamine, Bop / acetonitrile; dimethylformamide / 16 h / Ambient temperature

3: H₂, 1 N HCl / 10percent palladium hydroxide/C / tetrahydrofuran / 3 h

4: acetic acid, sodium cyanoborohydride / methanol / 2.25 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; hydrogen; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm950642a

upstream raw materials:

(S)-N-carbobenzoxy-tert-butylleucine

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride

Downstream raw materials:

(S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acid

(R^*)-N²-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl ester

(S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-4-methoxy-butyric acid tert-butyl ester

(S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-4-dimethylcarbamoyl-butyric acid tert-butyl ester