(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

Base Information

Chemical Name:(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester
CAS No.:367260-31-9
Molecular Formula:C₂₄H₃₄N₂O₆
Molecular Weight:446.544
Hs Code.:

Synonyms:(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

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Chemical Property of (S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

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Technology Process of (S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

There total 1 articles about (S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 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: 97.0%

: 109183-71-3
N-(tert-butoxycarbonyl)-L-cyclohexylglycine

: (S)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester hydrochloride

: 367260-31-9
(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

Guidance literature:: With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃;
DOI:10.1021/jm050520a

Reference yield:

: 367260-31-9
(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

: (S,S)-2-cyclohexylglycyl-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester hydrochloride

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(02)00511-2

Reference yield:

: 367260-31-9
(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

: 875628-51-6
{3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: HCl / dioxane / 4 h / 20 °C

2.1: 2.30 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

3.1: borane*THF / tetrahydrofuran / 1.67 h / 0 °C

3.2: 93 percent / aq. H₂O₂; ethanol / tetrahydrofuran / 2.33 h / 0 - 20 °C / pH 7

4.1: 66 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphine / CH₂Cl₂ / 82.33 h / 0 - 20 °C

5.1: 98 percent / aq. LiOH / methanol; tetrahydrofuran / 4 h / 0 - 20 °C

6.1: 66 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

7.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

8.1: 98 percent / H₂ / Pd/C / ethanol; methanol / 3 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; borane-THF; hydrogen; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Mitsunobu reaction / 7.1: Dess-Martin periodinane oxidation;
DOI:10.1021/jm050520a