(2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin

Base Information

• Chemical Name: (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin
• CAS No.: 46988-94-7
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.282
• Mol file: 46988-94-7.mol

Synonyms:(2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin

Chemical Property of (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-(S)-amino-(3-hydroxyphenyl)acetic acid 95+% ee ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin

There total 4 articles about (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin 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: 87.0%

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + (S)-3-hydroxyphenylglycine (71301-82-1) → (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin (46988-94-7,33130-90-4)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 23h; Ambient temperature;

Reference yield:

(2S)-(+)-2-(3-Methoxyphenyl)glycin (108647-55-8) → (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin (46988-94-7,33130-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 48percent HBr / 4 h / 130 - 140 °C

2: 87 percent / NEt₃ / H₂O; dioxane / 23 h / Ambient temperature

With hydrogen bromide; triethylamine; In 1,4-dioxane; water;

Reference yield:

(2S)-(+)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(3-methoxyphenyl)essigsaeure (108594-41-8) → (2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hdroxyphenyl)glycin (46988-94-7,33130-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / NaIO₄, 2N HCl / H₂O / 15 h / Ambient temperature

2: 70 percent / 48percent HBr / 4 h / 130 - 140 °C

3: 87 percent / NEt₃ / H₂O; dioxane / 23 h / Ambient temperature

With hydrogenchloride; sodium periodate; hydrogen bromide; triethylamine; In 1,4-dioxane; water;

upstream raw materials:

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

(S)-3-hydroxyphenylglycine

(2S)-(+)-2-(3-Methoxyphenyl)glycin

(2S)-(+)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(3-methoxyphenyl)essigsaeure

Downstream raw materials:

(S)-tert-Butoxycarbonylamino-(4-formyl-3-hydroxy-phenyl)-acetic acid

L-(+)-Forphenicin

forphenicinol

(2S)-(+)-N-tert-Butoxycarbonyl-2-(3-hydroxy-4-hydroxymethylphenyl)glycin

Refernces