tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate

Base Information

• Chemical Name: tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate
• CAS No.: 161644-46-8
• Molecular Formula: C₂₀H₂₇NO₄S
• Molecular Weight: 377.505
• Mol file: 161644-46-8.mol

Synonyms:

Chemical Property of tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate

There total 5 articles about tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate 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:

tert-butyl diethylphosphonoacetate (27784-76-5) + (R)-2,2-Dimethyl-3-(2-phenylsulfanyl-acetyl)-oxazolidine-4-carbaldehyde (1025965-41-6) → tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate (161644-46-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 ℃; for 3h; Yield given;

Reference yield:

(phenylthio)acetic acid (103-04-8) → tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate (161644-46-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / Et₃N, 4-dimethylaminopyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

2: 76 percent / p-toluenesulfonic acid, molecular sieves 4A / benzene / Heating

3: 92 percent / NaBH₄, LiI / tetrahydrofuran / Ambient temperature

4: SO₃-pyridine complex, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

5: N,N-diisopropylethylamine, LiCl / acetonitrile / 3 h / 0 °C

With dmap; sodium tetrahydroborate; pyridine-SO₃ complex; 4 A molecular sieve; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium chloride; lithium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

Reference yield:

N-(phenylthioacetyl)-D-serine methyl ester (161644-41-3) → tert-butyl (S)-3-<2,2-dimethyl-3-(phenylthioacetyl)oxazolidin-4-yl>-(E)-propenoate (161644-46-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / p-toluenesulfonic acid, molecular sieves 4A / benzene / Heating

2: 92 percent / NaBH₄, LiI / tetrahydrofuran / Ambient temperature

3: SO₃-pyridine complex, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

4: N,N-diisopropylethylamine, LiCl / acetonitrile / 3 h / 0 °C

With sodium tetrahydroborate; pyridine-SO₃ complex; 4 A molecular sieve; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

upstream raw materials:

tert-butyl diethylphosphonoacetate

(R)-2,2-Dimethyl-3-(2-phenylsulfanyl-acetyl)-oxazolidine-4-carbaldehyde

(phenylthio)acetic acid

N-(phenylthioacetyl)-D-serine methyl ester

Downstream raw materials:

tert-butyl (6S,7R,7aS)-5,6,7,7a-tetrahydro-3,3-dimethyl-5-oxo-6-phenylthio-1H,3H-pyrrolo<1,2-c>oxazol-7-ylacetate