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

Base Information

• Chemical Name: (R^*)-N²-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl ester
• CAS No.: 166169-85-3
• Molecular Formula: C₃₃H₄₄N₄O₇
• Molecular Weight: 608.735

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

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

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

There total 3 articles about (R^*)-N²-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl 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: 87.0%

L-glutamine t-butyl ester hydrochloride + (S)-1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinecarboxylic acid (166169-82-0) → (R*)-N2-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl ester (166169-85-3)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; for 16h; 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) → (R*)-N2-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl ester (166169-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 820 mg / LiOH / methanol; tetrahydrofuran / 4 h

2: 87 percent / BOP, DIEA / acetonitrile; dimethylformamide / 16 h

With lithium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm9507284

Reference yield:

(S)-N-carbobenzoxy-tert-butylleucine (62965-10-0) → (R*)-N2-<<1,2,3,4-tetrahydro-2-<3-methyl-N-<(phenylmethoxy)-carbonyl>-L-valyl>-3-isoquinolinyl>carbonyl>-L-glutamine, 1,1-dimethylethyl ester (166169-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / DIEA, BOP / CH₂Cl₂ / 16 h / 0 - 5 °C

2: 820 mg / LiOH / methanol; tetrahydrofuran / 4 h

3: 87 percent / BOP, DIEA / acetonitrile; dimethylformamide / 16 h

With lithium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm9507284

upstream raw materials:

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

(S)-N-carbobenzoxy-tert-butylleucine

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

Downstream raw materials:

(R*,S*)-N-<<2-amino>-3-<(triphenylmethyl)thio>propyl>-3-methyl-L-valyl>-1,2,3,4-tetrahydro-3-isoquinolinyl>carbonyl>-L-glutamine tert-butyl ester

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