N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide

Base Information

• Chemical Name: N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide
• CAS No.: 147200-03-1
• Molecular Formula: C10H14N2O5S3
• Molecular Weight: 338.43
• DSSTox Substance ID: DTXSID40440163
• Wikidata: Q72490331
• Mol file: 147200-03-1.mol

Synonyms:147200-03-1;N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide;N-[(4S,6S)-6-Methyl-7,7-dioxo-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl]acetamide;(4S)-4-Acetamide-5,6-Dihydro-6-Methyl-2-Sulfonamide-Thio[2,3-B]Thiopyran7,7Dioxide;N-[(4S,6S)-2-(Aminosulfonyl)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]acetami;C10H14N2O5S3;199734-58-2;SCHEMBL12315837;AMY8618;DTXSID40440163;BCP11929;MFCD12407171;AKOS015898774;AC-6912;N-6-Methyl-7,7-dioxo-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl]acetamide;Acetamide, N-[(4S,6S)-2-(aminosulfonyl)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]-;DS-17941;CS-0158165;FT-0771878;D70653;J-501481;N-((4S,6S)-6-Methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-4-yl)-acetamide;N-[(4S,6S)-6-Methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7lambda~6~-thieno[2,3-b]thiopyran-4-yl]acetamide;trans-(6S)-4-acetylamino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

Chemical Property of N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Refractive Index: 1.647
• PKA: 9.38±0.60(Predicted)
• PSA: 168.40000
• Density: 1.627 g/cm³
• LogP: 3.39140
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 338.00648507
• Heavy Atom Count: 20
• Complexity: 604

Purity/Quality:

99.9% ^*data from raw suppliers

N-[(4S,6S)-2-(Aminosulfonyl)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C2=C(S1(=O)=O)SC(=C2)S(=O)(=O)N)NC(=O)C
• Isomeric SMILES: C[C@H]1C[C@@H](C2=C(S1(=O)=O)SC(=C2)S(=O)(=O)N)NC(=O)C
• Uses: N-[(4S,6S)-2-(Aminosulfonyl)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]acetamide is used as a reagent in the synthesis of MK-0507, a topically-active carbonic anhydrase inhibitor.

Technology Process of N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide

There total 6 articles about N-((4S,6S)-6-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)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:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (154802-22-9) → (4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) + cis-(6S)-4-acetylammino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (147128-79-8,120298-38-6)

Guidance literature:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide; With methanesulfonic acid; In water; acetonitrile; at 10 - 87 ℃; for 19h; Inert atmosphere; Reflux;

With ammonium hydroxide; In water; acetonitrile; at 7 - 40 ℃; for 4h; pH=7.3; Overall yield = 91.1 %; Overall yield = 20.6 g; Optical yield = 58 %de;

Reference yield:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (154802-22-9) + acetonitrile (75-05-8,26809-02-9) → (4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) + cis-(6S)-4-acetylammino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (147128-79-8,120298-38-6)

Guidance literature:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide; acetonitrile; With methanesulfonic acid; at 10 - 87 ℃; for 18h; Inert atmosphere;

With ammonium hydroxide; water; at 7 - 40 ℃; for 4.5h; pH=7.3; Overall yield = 20.6 g;

Reference yield:

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one (147086-79-1) → (4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) + cis-(6S)-4-acetylammino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (147128-79-8,120298-38-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride; sulfuryl dichloride / 10 h / 28 °C / Inert atmosphere

2.1: ammonia / methanol; acetone / -10 °C / Inert atmosphere

3.1: sodium tungstate (VI) dihydrate / methanol; water / 47 h / 10 - 50 °C / Inert atmosphere

4.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 15 °C / Inert atmosphere

4.2: 2 h / 40 °C

5.1: methanesulfonic acid / water; acetonitrile / 19 h / 10 - 87 °C / Inert atmosphere; Reflux

5.2: 4 h / 7 - 40 °C / pH 7.3

With sodium tetrahydroborate; thionyl chloride; sulfuryl dichloride; sodium tungstate (VI) dihydrate; methanesulfonic acid; ammonia; In tetrahydrofuran; methanol; water; acetone; acetonitrile;

upstream raw materials:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

(S)-6-methyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonyl chloride

(6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide

Downstream raw materials:

dorzolamide hydrochloride

dorzolamide

Refernces

• 1、 -. "PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED OXAMIDES". Page/Page column 13; 14. . Retrieved 2014/01/18.