Dimethylformamide → Dimethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester

HRID 356555Notes

Reaction equation

HRID 356555 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[C:8]([CH3:18])=[CH:7][C:6]=1[S:19]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[OH:30][C:31]1[CH2:36][C:35]([CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=2)([CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)[O:34][C:33](=[O:55])[CH:32]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CO.C(Cl)(Cl)Cl>[C:1]([C:5]1[C:6]([S:19][C:32]2[C:33](=[O:55])[O:34][C:35]([CH2:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([OH:45])=[CH:43][CH:44]=3)([CH2:46][CH2:47][C:48]3[CH:49]=[CH:50][C:51]([OH:54])=[CH:52][CH:53]=3)[CH2:36][C:31]=2[OH:30])=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:16])(=[O:17])[N:13]([CH3:15])[CH3:14])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10695175toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) esterHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 54688040Dimethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a round bottom flask equipped with a magnetic stirrer were added toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example UUU; 0.128 g, 0.280 mmol), 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP; 0.100 g, 0.280 mmol), K2CO3 (0.154 g, 1.12 mmol), and DMF (8 mL), as described in General Method 9. The slurry was stirred at room temperature overnight. After standard work-up, the residue was submitted to flash chromatography (97% CHCl3 :3% MeOH) to yield the title compound, m.p. 139° C. 1H NMR (CDCl3) δ 1.53 (s, 9 H), 1.91 (s, 3 H), 2.11 (m, 4 H), 2.65 (m, 4 H), 2.86 (s, 2 H), 2.98 (s, 6 H), 4.80 (br s, 2 H), 6.72 (s, 1 H), 6.73 (d, 4 H), 6.98 (d, 4 H), 7.27 (s, 1 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer

Sources & evidence

ORD record
ord-2ab1718eca364b1ca7ce43f569e9a17b
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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