4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester

Base Information

• Chemical Name: 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester
• CAS No.: 628724-19-6
• Molecular Formula: C₄₂H₄₄Cl₂N₂O₈
• Molecular Weight: 775.726
• Mol file: 628724-19-6.mol

Synonyms:4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester

Chemical Property of 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester

There total 1 articles about 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl 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: 93.0%

Fmoc-Nα-methylglutamine t-butyl ester (200616-40-6) + (S)-O-(2,6-dichlorobenzyl)tyrosine methyl ester → 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester (628724-19-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0960-894X(03)00760-1

Reference yield: 72.0%

benzenesulfonyl chloride (98-09-9) + 4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester (628724-19-6) → (S)-4-(Benzenesulfonyl-methyl-amino)-4-{(S)-2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-butyric acid tert-butyl ester (628724-20-9)

Guidance literature:

4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester; With diethylamine; In dichloromethane;

benzenesulfonyl chloride; With 4-methyl-morpholine; In dichloromethane;

DOI:10.1016/S0960-894X(03)00760-1

Reference yield:

4-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-4-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-butyric acid tert-butyl ester (628724-19-6) → (S)-4-(Benzenesulfonyl-methyl-amino)-4-{(S)-1-carboxy-2-[4-(2,6-dichloro-benzyloxy)-phenyl]-ethylcarbamoyl}-butyric acid

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₂NH / CH₂Cl₂

1.2: 72 percent / NMM / CH₂Cl₂

2.1: aq. LiOH / tetrahydrofuran / 2 h

2.2: 86 percent / aq. TFA

With lithium hydroxide; diethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(03)00760-1

upstream raw materials:

Fmoc-N^α-methylglutamine t-butyl ester

Downstream raw materials:

(S)-4-(Benzenesulfonyl-methyl-amino)-4-{(S)-2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-butyric acid tert-butyl ester