Potassium Carbonate → Dimethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(3-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

HRID 356551Notes

Reaction equation

HRID 356551 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[C:27]([C:31]1[CH:36]=[C:35]([O:37][S:38](=[O:43])(=[O:42])[N:39]([CH3:41])[CH3:40])[C:34]([CH3:44])=[CH:33][C:32]=1[S:45]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:27]([C:31]1[C:32]([S:45][C:3]2[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=3)[CH2:7][C:2]=2[OH:1])=[CH:33][C:34]([CH3:44])=[C:35]([O:37][S:38](=[O:42])(=[O:43])[N:39]([CH3:40])[CH3:41])[CH:36]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10695175toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) esterHCID 546822904-Hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 54688038Dimethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(3-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was synthesized following General Method 9 and using 77 mg (0.2 mmol) of 4-hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example XX), 100 mg (0.2 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example UUU), 18 mg (0.8 mmol) of K2CO3 and 5 mL of DMF. The reaction was worked up as described and chromatographed on silica gel, eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to give the title compound. 1H NMR (DMSO-d6) δ 1.45 (s, 9 H), 1.9 (s, 3 H), 2.95 (m, 4 H), 2.6 (m, 4 H), 2.95 (s, 6 H), 3.35 (m, 2 H), 6.60 (m, 6 H), 6.8 (s, 1 H), 7.05 (t, 2 H), 7.15 (s, 1 H), 9.25 (s, 2 H).

Workup

  1. customThe compound was synthesized
  2. customchromatographed on silica gel
  3. washeluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)

Sources & evidence

ORD record
ord-539911fad2d046b3a6de0d172b5e0770
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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