(2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Base Information

• Chemical Name: (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid
• CAS No.: 192061-02-2
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.309
• Mol file: 192061-02-2.mol

Synonyms:(2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Chemical Property of (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

There total 6 articles about (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid 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: 86.0%

(2S-cis)-methyl ester 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-01-1) → (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-02-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(97)00865-4

Reference yield:

cis-3-[[(4-methoxyphenyl)methoxy]methyl]-oxiranemethanol → (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 15.0 g

2: 86 percent / TBAF / tetrahydrofuran / 0.5 h

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 2: Substitution;

DOI:10.1016/S0040-4020(99)01046-7

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 58 percent / p-TsOH / benzene / Heating

2: 78 percent / LiAlH₄, AlCl₃ / tetrahydrofuran / from 0 deg C to RT

3: 75 percent / Ti(OiPr)4, L-(+)-DET, tBuOOH / CH₂Cl₂ / -20 °C

4: 1.) NaN₃, NH₄Cl; 2.) Et₃N, DMAP; 3.) Ph₃P

5: 86 percent / TBAF / tetrahydrofuran / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; aluminium trichloride; sodium azide; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; ammonium chloride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(97)00865-4

upstream raw materials:

(2S-cis)-methyl ester 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

4-methoxy-benzaldehyde

2-(4-methoxyphenyl)-4,7-dihydro-1,3-dioxepine

(Z)-4-(4-methoxybenzyloxy)but-2-en-1-ol

Downstream raw materials:

(2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1,5-dimethyl ester 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-1H-aziridino[2,3-c][1]benzazocine-1,3,5(2H)-tricarboxylic acid

[2S-(2α,3α)]-methyl ester 2-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-[[(4-methoxyphenyl)methoxy]methyl]-1-aziridinecarboxylic acid

[2S-(2α,3α)]-methyl ester 2-[1-hydroxy-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-[[(4-methoxyphenyl)methoxy]methyl]-1-aziridinecarboxylic acid