{4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride

Base Information

• Chemical Name: {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride
• CAS No.: 135703-83-2
• Molecular Formula: C₂₇H₄₀N₄O₅S*ClH
• Molecular Weight: 569.165

Synonyms:

Chemical Property of {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride

Chemical Property:

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Technology Process of {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride

There total 6 articles about {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride 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:

ethyl 2-amino-α-(hydroxyimino)-4-thiazole acetate (60845-81-0) → {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride (135703-83-2,142185-75-9,142185-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂, HCl / 10percent Pd/C / ethanol

2: aq. K₂CO₃ / tetrahydrofuran / 24 h / Ambient temperature

3: aq. sodium bicarbonate / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

4: aq. KOH / ethanol / 1.5 h / Ambient temperature

5: 6.0 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

6: 5.5 g / HCl (gas) / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

Reference yield:

{4-[tert-Butoxycarbonylamino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester (135703-82-1,142185-73-7,142185-74-8) → {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride (135703-83-2,142185-75-9,142185-76-0)

Guidance literature:

With hydrogenchloride; In methanol; Ambient temperature;

DOI:10.1021/jm00092a006

Reference yield:

ethyl 2-amino-α-(N-(t-butoxycarbonyl)amino)-4-thiazoleacetate (60846-29-9) → {4-[Amino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester; hydrochloride (135703-83-2,142185-75-9,142185-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. sodium bicarbonate / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

2: aq. KOH / ethanol / 1.5 h / Ambient temperature

3: 6.0 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

4: 5.5 g / HCl (gas) / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

upstream raw materials:

{4-[tert-Butoxycarbonylamino-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-methyl]-thiazol-2-yl}-carbamic acid benzyl ester

ethyl 2-amino-α-(N-(t-butoxycarbonyl)amino)-4-thiazoleacetate

α-(2-benzyloxycarbonylaminothiazol-4-yl)-α-(t-butoxycarbonylamino)acetic acid

ethyl α-amino-α-(2-aminothiazol-4-yl)acetate dihydrochloride

Downstream raw materials:

<1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide

(4-{((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-methyl}-thiazol-2-yl)-carbamic acid benzyl ester

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