methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate

Base Information

• Chemical Name: methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate
• CAS No.: 267007-61-4
• Molecular Formula: C₂₁H₃₁ClN₂O₆
• Molecular Weight: 442.94

Synonyms:methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate

Chemical Property of methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate

Chemical Property:

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Technology Process of methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate

There total 5 articles about methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate 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: 81.0%

methanol (67-56-1) + (S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one (210533-60-1) → methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate (267007-61-4)

Guidance literature:

With silver trifluoroacetate; In triethylamine; at 20 ℃; for 3h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<16::AID-HLCA16>3.0.CO;2-3

Reference yield:

Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) → methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate (267007-61-4)

Guidance literature:

Multi-step reaction with 4 steps

1: ClCO₂Et; Et₃N / tetrahydrofuran

2: diethyl ether

3: 89 percent / Et₃N; H₂O / CF₃CO₂Ag / tetrahydrofuran

With water; chloroformic acid ethyl ester; triethylamine; silver trifluoroacetate; In tetrahydrofuran; diethyl ether; 1: Chlorination / 2: Methylation / 3: Wolff rearrangement / 4: Esterification;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1223::AID-ANIE1223>3.0.CO;2-A

Reference yield:

(S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one (210533-60-1) → methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoate (267007-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃N; H₂O / CF₃CO₂Ag / tetrahydrofuran

With water; triethylamine; silver trifluoroacetate; In tetrahydrofuran; 1: Wolff rearrangement / 2: Esterification;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1223::AID-ANIE1223>3.0.CO;2-A

upstream raw materials:

methanol

(S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid

(S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one

Boc-(S)-Lys(2-Cl-Z)-OH

Downstream raw materials:

cyclo(β³-HTrp-β³-HPhe-β³-HThr(OBn)-β³-HLys(N^ε-2-Cl-Z))

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