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

Base Information

• Chemical Name: (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid
• CAS No.: 219967-67-6
• Molecular Formula: C₂₀H₂₉ClN₂O₆
• Molecular Weight: 428.913

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid 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: 91.0%

(S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one (210533-60-1) → (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid (219967-67-6)

Guidance literature:

With silver trifluoroacetate; In tetrahydrofuran; water; 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) → (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid (219967-67-6)

Guidance literature:

Multi-step reaction with 3 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;

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

Reference yield:

(5-tert-butoxycarbonylamino-5-chlorocarbonyl-pentyl)-carbamic acid 2-chloro-benzyl ester → (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid (219967-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: 89 percent / Et₃N; H₂O / CF₃CO₂Ag / tetrahydrofuran

With water; triethylamine; silver trifluoroacetate; In tetrahydrofuran; diethyl ether; 1: Methylation / 2: Wolff rearrangement;

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

upstream raw materials:

(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:

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

Boc-β³hLys(2-Cl-Cbz)-β³hPhe-OBn

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

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