Triethylamine → 6-[-2-(4-Fluoro-phenyl)-ethyl]-4-hydroxy-6-isopropyl-3-(5-isopropyl-benzothiazol-6-ylsulfanyl)-5,6-dihydro-pyran-2-one

HRID 23511Notes

Reaction equation

HRID 23511 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH:18]([CH3:20])[CH3:19])[O:15][C:14](=[O:16])[CH:13]=[C:12]([OH:17])[CH2:11]2)=[CH:4][CH:3]=1.[CH:21]([C:24]1[C:25]([S:33]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:26][C:27]2[S:31][CH:30]=[N:29][C:28]=2[CH:32]=1)([CH3:23])[CH3:22].CCN(CC)CC>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2([CH:18]([CH3:20])[CH3:19])[O:15][C:14](=[O:16])[C:13]([S:33][C:25]3[C:24]([CH:21]([CH3:23])[CH3:22])=[CH:32][C:28]4[N:29]=[CH:30][S:31][C:27]=4[CH:26]=3)=[C:12]([OH:17])[CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 546770156-[(4-Fluoro-phenyl)-ethyl]-4-hydroxy-6-isopropyl-5,6-dihydropyran-2-oneHCID 69734629toluene-4-thiosulfonic acid S-(5-isopropyl-benzothiazol-6-yl)ester

Product 1

HCID 697347296-[-2-(4-Fluoro-phenyl)-ethyl]-4-hydroxy-6-isopropyl-3-(5-isopropyl-benzothiazol-6-ylsulfanyl)-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to General Method 16b using 6-[(4-fluoro-phenyl)-ethyl]-4-hydroxy-6-isopropyl-5,6-dihydropyran-2-one (Example E-27; 0.5 g, 1.8 mmol), toluene-4-thiosulfonic acid S-(5-isopropyl-benzothiazol-6-yl)ester (Example BB-4; 0.65 g, 1.8 mmol), NEt3 (0.22 g, 2.16 mmol), and acetonitrile (10 mL). The crude compound was purified by flash silica gel chromatography (25% EtOAc in hexanes to 100% EtOAc to 5% MeOH in EtOAc as eluents), mp 104-105° C. MS (APCI): 486.

Workup

  1. customThe crude compound was purified by flash silica gel chromatography (25% EtOAc in hexanes to 100% EtOAc to 5% MeOH in EtOAc as eluents), mp 104-105° C

Sources & evidence

ORD record
ord-d54e21561ad6407cbc62f789fd009f4d
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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