(S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 752251-04-0
• Molecular Formula: C₂₆H₃₇N₃O₆
• Molecular Weight: 487.596
• Mol file: 752251-04-0.mol

Synonyms:(S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property of (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

There total 4 articles about (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic 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: 58.0%

BOC-O-benzyl-L-serine (23680-31-1) + 4-((S)-2-Amino-3-dimethylamino-propyl)-benzene-1,2-diol (862695-37-2) → (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester (752251-04-0)

Guidance literature:

BOC-O-benzyl-L-serine; With triethylamine; isobutyl chloroformate; In tetrahydrofuran; cooling;

4-((S)-2-Amino-3-dimethylamino-propyl)-benzene-1,2-diol; In tetrahydrofuran; at -20 - 10 ℃; for 3h;

DOI:10.1002/anie.200453909

Reference yield:

levodopa (59-92-7,90638-38-3) → (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester (752251-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. NaOH / dioxane / 16 h / 20 °C

2.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.5 h / -35 °C

2.2: 5.0 g / tetrahydrofuran / 20 °C

3.1: TFA / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

5.1: i-BuOCOCl; Et₃N / tetrahydrofuran / cooling

5.2: 58 percent / tetrahydrofuran / 3 h / -20 - 10 °C

With 4-methyl-morpholine; sodium hydroxide; borane-THF; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1002/anie.200453909

Reference yield:

2-amino-3-(3,4-dihydroxy-phenyl)-N,N-dimethyl-propionamide → (S,S)-{2-benzyloxy-1-[1-(3,4-dihydroxy-benzyl)-2-dimethylamino-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester (752251-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

2.1: i-BuOCOCl; Et₃N / tetrahydrofuran / cooling

2.2: 58 percent / tetrahydrofuran / 3 h / -20 - 10 °C

With borane-THF; triethylamine; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1002/anie.200453909

upstream raw materials:

BOC-O-benzyl-L-serine

4-((S)-2-Amino-3-dimethylamino-propyl)-benzene-1,2-diol

levodopa

(S)-[2-(3,4-dihydroxy-phenyl)-1-dimethylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

(S)-3-amino-6,7-bis(OBn)-1,1-dimethyl-1,2,3,4-tetrahydroquinolin-1-ium L-ser(OBn)-D-ser (OBn)-BocL-thr(OBn)

H-L-Thr(OBn)-D-Ser(OBn)-LSer(OBn)-(3S)-THQ(OBn)

(2S,3S)-6,7-bis-benzyloxy-3-(3-benzyloxy-2-tert-butoxycarbonylaminopropionylamino)-1,1-dimethyl-1,2,3,4-tetrahydroquinolinium

(S)-3-((S)-2-Amino-3-benzyloxy-propionylamino)-6,7-bis-benzyloxy-1,1-dimethyl-1,2,3,4-tetrahydro-quinolinium