tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate

Base Information

• Chemical Name: tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate
• CAS No.: 857083-14-8
• Molecular Formula: C₄₇H₆₅N₅O₇
• Molecular Weight: 812.062
• Mol file: 857083-14-8.mol

Synonyms:tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate

Chemical Property of tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate

There total 6 articles about tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate 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: 21.0%

(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-(tert-butoxy)phenyl]pent-4-enoic acid (857083-12-6) + N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate (857083-14-8)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 - 50 ℃; for 72h;

DOI:10.1021/jm050059m

Reference yield:

(4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one (857083-09-1) → tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate (857083-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: PhSCu / diethyl ether; tetrahydrofuran / -40 °C

1.2: 41 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 288 mg / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: 88 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

4.1: 21 percent / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; copper(I) thiophenolate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

Reference yield:

(3R,4S)-3-[(tert-butoxy)phenyl]pent-4-enoyl-4-phenyl-1,3-oxazolidin-2-one (857083-10-4) → tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate (857083-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 288 mg / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 88 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

3.1: 21 percent / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

upstream raw materials:

(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-(tert-butoxy)phenyl]pent-4-enoic acid

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

(4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one

(3R,4S)-3-[(tert-butoxy)phenyl]pent-4-enoyl-4-phenyl-1,3-oxazolidin-2-one

Downstream raw materials:

tert-butyl 2-{(9S,10S,18S,14R)-7,16,19-triaza-10-[4-(tert-butoxy)phenyl]-18-(carbamoylmethyl)-14-[(5-methylindolyl)methyl]-8,17,20-trioxospiro[5.14]icos-11-en-9-yl}acetate