Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid

Base Information

• Chemical Name: Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid
• CAS No.: 135761-10-3
• Molecular Formula: CH₄O₃S*C₁₄H₁₇NO₃S
• Molecular Weight: 375.467
• Mol file: 135761-10-3.mol

Synonyms:

Chemical Property of Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid

There total 10 articles about Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic 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:

methanesulfonic acid (75-75-2,98527-29-8) + (4R,5R)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazoline (135761-13-6) → Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid (135761-10-3,135761-12-5)

Guidance literature:

With acetic anhydride; In chloroform; at 35 ℃; for 0.333333h;

DOI:10.1021/jo00021a028

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine (135204-55-6) → Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid (135761-10-3,135761-12-5)

Guidance literature:

With acetic anhydride; In chloroform; at 35 ℃; for 16h;

DOI:10.1021/jo00021a028

Reference yield:

(1S,2S)-(+)-thiomicamine (16854-32-3) → Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid (135761-10-3,135761-12-5)

Guidance literature:

Multi-step reaction with 8 steps

1: toluene / 18 h / Heating

2: Et₃N / CH₂Cl₂ / 3 h / 15 °C

3: K₂CO₃, MeOH / 1 h / 25 °C

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, a) -60 deg C, 15 min, b) up to -50 deg C, 2) a) -50 deg C, 20 min, b) up to 0 deg C, 2 h

5: DABCO / 3 h / 35 °C

6: NaBH₄, CaCl₂ / tetrahydrofuran; ethanol / 2 h / 5 °C

7: Et₃N / CH₂Cl₂ / 1 h / 15 °C

8: Ac₂O / CHCl₃ / 16 h / 35 °C

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; sodium tetrahydroborate; oxalyl dichloride; acetic anhydride; potassium carbonate; dimethyl sulfoxide; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jo00021a028

upstream raw materials:

methanesulfonic acid

(4R,5R)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazoline

(4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

(1S,2S)-(+)-thiomicamine

Downstream raw materials:

(4R,5R)-4-(acetoxymethyl)-5-<4-(methylthio)phenyl>-2-methyl-1,3-oxazoline

(4R,5S)-4-(acetoxymethyl)-5-<4-(methylthio)phenyl>-2-methyl-1,3-oxazoline

(R*,R*)-(+)-thiomicamine

(+)-(1S,2R)-2-amino-1-<4-(methylthio)phenyl>-1,3-propanediol

Refernces