(S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester

Base Information

• Chemical Name: (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester
• CAS No.: 325464-82-2
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Mol file: 325464-82-2.mol

Synonyms:(S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester

Chemical Property of (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester

There total 1 articles about (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl 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:

glyoxylic acid ethyl ester (924-44-7) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → (S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester (325464-82-2) + (R)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester

Guidance literature:

With 2,2'-isopropylidenebis<(4S)-4-tert-butyl-4,5-dihydrooxazole>; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 24h; Further Variations:; Solvents; Product distribution;

DOI:10.1055/s-2003-39176

Reference yield:

(S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester (325464-82-2) → (R)-mandelic acid ethyl ester (10606-72-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: PhI=O; TMSN₃ / CH₂Cl₂ / 4 h / -78 °C

3: 28 mg / aq. NaHCO₃ / tetrahydrofuran; CH₂Cl₂ / 48 h / 20 °C

4: NOBF₄ / CH₂Cl₂ / 0.17 h / 0 °C

5: 14 mg / H₃PO₂ / Cu₂O / 0.25 h / 0 °C

6: aq. HCl / ethanol / 12 h / 20 °C

With hydrogenchloride; trimethylsilylazide; iodosylbenzene; hypophosphorous acid; sodium hydrogencarbonate; nitrosonium tetrafluoroborate; triethylamine; copper(I) oxide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja002593j

Reference yield:

(S)-2-[4-(dimethylamino)phenyl]-2-hydroxyacetic acid ethyl ester (325464-82-2) → (S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester (135348-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: PhI=O; TMSN₃ / CH₂Cl₂ / 4 h / -78 °C

3: 28 mg / aq. NaHCO₃ / tetrahydrofuran; CH₂Cl₂ / 48 h / 20 °C

4: NOBF₄ / CH₂Cl₂ / 0.17 h / 0 °C

5: 14 mg / H₃PO₂ / Cu₂O / 0.25 h / 0 °C

With trimethylsilylazide; iodosylbenzene; hypophosphorous acid; sodium hydrogencarbonate; nitrosonium tetrafluoroborate; triethylamine; copper(I) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja002593j

upstream raw materials:

glyoxylic acid ethyl ester

N,N-dimethyl-aniline

Downstream raw materials:

(R)-mandelic acid ethyl ester

(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester

(S)-(-)-ethyl mandelate

(S)-(4-amino-phenyl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester