Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI)

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI)
• CAS No.: 139561-08-3
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.19924
• Mol file: 139561-08-3.mol

Synonyms:Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI)

Chemical Property of Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI)

Chemical Property:

• PSA: 83.55000
• LogP: 1.36190

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI)

There total 20 articles about Cyclopropanecarboxylic acid, 1-amino-2-(3-hydroxyphenyl)-, (1S-cis)- (9CI) 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:

(-)-N-<(1,1-dimethylethoxy)carbonyl>-O-<(2-methoxyethoxy)methyl>-(Z)-2,3-methano-m-tyrosine (139561-04-9) → (-)-(Z)-2,3-methano-m-tyrosine (139561-08-3)

Guidance literature:

With hydrogenchloride; Amberlite IRA-400 OH; acetic acid; 3-methyl-phenol; In 1,4-dioxane; at 0 ℃; Yield given;

DOI:10.1021/jm00086a009

Reference yield:

meta-hydroxybenzaldehyde (100-83-4) → (-)-(Z)-2,3-methano-m-tyrosine (139561-08-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / aq. NaOH, Aliquat 336 / CH₂Cl₂ / Ambient temperature

2: 89 percent / piperidine, acetic acid / toluene / Heating

3: 1.) NaH / 1.) DMSO, RT, 30 min, 2.) THF a) RT, 1 h, b) 50 - 60 deg C, 1 h

4: 95.6 percent / aq. NaOH / ethanol / 40 h / Ambient temperature

5: 1.) KOH, 2.) aq. N₂NNH₂ / 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 36 h

6: 39 percent / NaNO₂, 1 M aq. H₂SO₄ / 2.5 h / 0 - 4 °C

7: 89 percent / aq. KOH, carbitol / diethyl ether

8: 87 percent / 48 h / Heating

9: 85 percent / aq. NaOH / ethanol / Ambient temperature

10: 86 percent / various solvent(s); hexane / 6 h / Ambient temperature

11: 1.) m-cresol, 4 N aq. HCl, 2.) 3percent aq. CH₃COOH, Amberlite IRA-400 OH / dioxane / 0 °C

With piperidine; hydrogenchloride; potassium hydroxide; sodium hydroxide; azido amine; ethoxyethoxyethanol; Amberlite IRA-400 OH; sulfuric acid; Aliquat 336; sodium hydride; acetic acid; 3-methyl-phenol; sodium nitrite; In 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; toluene;

DOI:10.1021/jm00086a009

Reference yield:

(3-methoxyethoxymethyloxy)benzaldehyde (139461-72-6) → (-)-(Z)-2,3-methano-m-tyrosine (139561-08-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / piperidine, acetic acid / toluene / Heating

2: 1.) NaH / 1.) DMSO, RT, 30 min, 2.) THF a) RT, 1 h, b) 50 - 60 deg C, 1 h

3: 95.6 percent / aq. NaOH / ethanol / 40 h / Ambient temperature

4: 1.) KOH, 2.) aq. N₂NNH₂ / 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 36 h

5: 39 percent / NaNO₂, 1 M aq. H₂SO₄ / 2.5 h / 0 - 4 °C

6: 89 percent / aq. KOH, carbitol / diethyl ether

7: 87 percent / 48 h / Heating

8: 85 percent / aq. NaOH / ethanol / Ambient temperature

9: 86 percent / various solvent(s); hexane / 6 h / Ambient temperature

10: 1.) m-cresol, 4 N aq. HCl, 2.) 3percent aq. CH₃COOH, Amberlite IRA-400 OH / dioxane / 0 °C

With piperidine; hydrogenchloride; potassium hydroxide; sodium hydroxide; azido amine; ethoxyethoxyethanol; Amberlite IRA-400 OH; sulfuric acid; sodium hydride; acetic acid; 3-methyl-phenol; sodium nitrite; In 1,4-dioxane; diethyl ether; ethanol; hexane; toluene;

DOI:10.1021/jm00086a009

upstream raw materials:

(-)-N-<(1,1-dimethylethoxy)carbonyl>-O-<(2-methoxyethoxy)methyl>-(Z)-2,3-methano-m-tyrosine

meta-hydroxybenzaldehyde

(3-methoxyethoxymethyloxy)benzaldehyde

diethyl <3-<(2-methoxyethoxy)methoxy>benzal>malonate