methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate

Base Information

• Chemical Name: methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate
• CAS No.: 1287261-40-8
• Molecular Formula: C₃₁H₄₁N₃O₈
• Molecular Weight: 583.682

Synonyms:methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate

Chemical Property of methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate

Chemical Property:

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Technology Process of methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate

There total 9 articles about methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate 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: 59.0%

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + (S)-methyl 2-((3-((4-methoxyphenyl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy) acetate (1287261-33-9) → methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate (1287261-40-8)

Guidance literature:

N-(tert-butyloxycarbonyl)-L-isoleucine; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.25h;

(S)-methyl 2-((3-((4-methoxyphenyl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy) acetate; In tetrahydrofuran; for 8h;

DOI:10.1021/jm101605z

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + di-tert-butyl dicarbonate (24424-99-5) → methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate (1287261-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide

2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / tetrahydrofuran

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; sodium hydroxide; In tetrahydrofuran;

DOI:10.1039/c3ra43249a

Reference yield:

(S)-tert-butyl 7-(2-methoxy-2-oxoethoxy)-3-((4-methoxyphenyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1223620-63-0) → methyl 2-((S)-2-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)-3-(4-methoxyphenylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yloxy)acetate (1287261-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; trifluoroacetic acid / dichloromethane

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / tetrahydrofuran / 0.25 h / 20 °C

2.2: 8 h

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm101605z

upstream raw materials:

(S)-tert-butyl 7-(2-methoxy-2-oxoethoxy)-3-((4-methoxyphenyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

(S)-tert-butyl 7-hydroxy-3-((4-methoxyphenyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

N-(tert-butyloxycarbonyl)-L-isoleucine

(S)-methyl 2-((3-((4-methoxyphenyl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy) acetate

Downstream raw materials:

tert-butyl (2S,3S)-1-((S)-7-(2-(hydroxyamino)-2-oxoethoxy)-3-(4-methoxyphenylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-methyl-1-oxopentan-2-yl carbamate

(S)-2-((2S,3S)-2-amino-3-methylpentanoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-N-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide hydrochloride

(S)-2-((2S,3S)-2-(3,3-dimethylbutanamido)-3-methylpentanoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-N-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

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