(1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid

Base Information

• Chemical Name: (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid
• CAS No.: 251320-39-5
• Molecular Formula: C₂₃H₃₄ClN₃O₆S
• Molecular Weight: 516.058

Synonyms:(1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid

Chemical Property of (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid

Chemical Property:

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Technology Process of (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid

There total 7 articles about (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic 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: 95.0%

methyl (1'S,4S)-2-[1-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylate (251320-38-4) → (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid (251320-39-5)

Guidance literature:

With sodium hydroxide; In methanol; for 1h;

DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) → (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid (251320-39-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / BOP; DIEA / CH₂Cl₂ / 1 h / 20 °C

2.1: 80 percent / imidazole / dimethylformamide / 0.5 h

3.1: 3.70 g / Lawesson reagent / dioxane / 0.67 h / 70 °C

4.1: 85 percent / 1N Bu₄NF / tetrahydrofuran / 0.42 h

5.1: 80 percent / PPh₃; DEAD / tetrahydrofuran / 0.25 h

6.1: acetonitrile / 0.5 h

6.2: NaBH₄ / methanol / 0.08 h / 0 °C

7.1: 95 percent / 1N NaOH / methanol / 1 h

With Lawessons reagent; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Acylation / 2.1: silylation / 3.1: sulfurization / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Methylation / 6.2: Reduction / 7.1: Hydrolysis;

DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

methyl (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-2-thiazoline-4-carboxylate (251320-37-3) → (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid (251320-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetonitrile / 0.5 h

1.2: NaBH₄ / methanol / 0.08 h / 0 °C

2.1: 95 percent / 1N NaOH / methanol / 1 h

With sodium hydroxide; In methanol; acetonitrile; 1.1: Methylation / 1.2: Reduction / 2.1: Hydrolysis;

DOI:10.1016/S0040-4020(99)00689-4

upstream raw materials:

methyl (1'S,4S)-2-[1-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylate

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

methyl (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-2-thiazoline-4-carboxylate

methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate

Downstream raw materials:

[N^α-(tert-butyloxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysinal

{(S)-5-[(S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-hexanoylamino)-propionylamino]-3-methyl-butyrylamino}-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-6-oxo-hexyl}-carbamic acid 2-chloro-benzyl ester

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