N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide

Base Information

• Chemical Name: N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide
• CAS No.: 6070-70-8
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.169
• DSSTox Substance ID: DTXSID30366666
• Wikidata: Q82152000
• Mol file: 6070-70-8.mol

Synonyms:325693-65-0;6070-70-8;N-(2-hydroxyethyl)-2-({3-oxo-4-phenyl-8-thia-4,6-diazatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),5-trien-5-yl}sulfanyl)acetamide;CBMicro_032822;Oprea1_518902;Oprea1_821861;N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide;DTXSID30366666;STL079444;AKOS000531735;N-(2-hydroxyethyl)-2-((4-oxo-3-phenyl-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)thio)acetamide;BIM-0032939.P001;F0739-0009;N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide

Chemical Property of N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 415.10243389
• Heavy Atom Count: 28
• Complexity: 624

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2=C(C1)C3=C(S2)N=C(N(C3=O)C4=CC=CC=C4)SCC(=O)NCCO

Technology Process of N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide

There total 8 articles about N-(2-hydroxyethyl)-2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide 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:

→ 3-Ethyl-5-oxo-pyrrolidin-2-carbonsaeure (2446-06-2,6070-70-8,531539-38-5)

Guidance literature:

3-Ethyl-5-oxo-pyrrolidin-2,2,4-tricarbonsaeure-triethylester, 1. Δ (in cc. HCl, Siedetemp.), 2. Δ (kurzzeitig, 200-220grad);

DOI:10.1021/jm00328a022

Reference yield:

L-Pyroglutamic acid (98-79-3) → (2S,3S)-3-ethyl-5-oxo-pyrrolidine-2-carboxylic acid (6070-70-8,531539-38-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 75 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: 1,4-diazabicyclooctane; butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 39 percent / tetrahydrofuran / -78 - 20 °C

3.1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

4.1: HMDS; butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: phenylselenenyl chloride / tetrahydrofuran / -78 - 20 °C

4.3: 48 percent / 1,4-diazabicyclooctane; m-chloroperbenzoic acid / tetrahydrofuran; CH₂Cl₂ / -20 - 20 °C

5.1: 62 percent / CuBr*S(CH₃)2; trimethylsilyl chloride / diethyl ether; tetrahydrofuran / -78 - -20 °C

6.1: H₂ / Pd/C / ethyl acetate; methanol / 2 h / 3000.24 Torr

7.1: 0.15 g / trifluoroacetic acid / CH₂Cl₂; H₂O / 1 h

With dmap; n-butyllithium; chloro-trimethyl-silane; 1,4-diazabicyclooctane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(02)01490-4

Reference yield:

(2S)-5-oxo-pyrrolidine-2-carboxylic acid 3-methyl-oxetan-3-ylmethyl ester (531539-21-6) → (2S,3S)-3-ethyl-5-oxo-pyrrolidine-2-carboxylic acid (6070-70-8,531539-38-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,4-diazabicyclooctane; butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 39 percent / tetrahydrofuran / -78 - 20 °C

2.1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

3.2: phenylselenenyl chloride / tetrahydrofuran / -78 - 20 °C

3.3: 48 percent / 1,4-diazabicyclooctane; m-chloroperbenzoic acid / tetrahydrofuran; CH₂Cl₂ / -20 - 20 °C

4.1: 62 percent / CuBr*S(CH₃)2; trimethylsilyl chloride / diethyl ether; tetrahydrofuran / -78 - -20 °C

5.1: H₂ / Pd/C / ethyl acetate; methanol / 2 h / 3000.24 Torr

6.1: 0.15 g / trifluoroacetic acid / CH₂Cl₂; H₂O / 1 h

With n-butyllithium; chloro-trimethyl-silane; 1,4-diazabicyclooctane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; hydrogen; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(02)01490-4

upstream raw materials:

L-Pyroglutamic acid

(2S)-5-oxo-pyrrolidine-2-carboxylic acid 3-methyl-oxetan-3-ylmethyl ester

(2S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

(2S)-1-benzyloxycarbonyl-5-oxo-pyrrolidine-2-carboxylic acid 2-(3-methyl-oxetan-3-yl-methyl) ester