Potassium Carbonate → N-Ethylsulfamic acid, 5-tert-butyl-4-{6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester

HRID 1003893Notes

Reaction equation

HRID 1003893 reaction equation
[CH:1]1([C:7]2([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[O:12][C:11](=[O:13])[CH:10]=[C:9]([OH:14])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([C:28]1[CH:33]=[C:32]([O:34][S:35](=[O:40])(=[O:39])[NH:36][CH2:37][CH3:38])[C:31]([CH3:41])=[CH:30][C:29]=1[S:42]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:24]([C:28]1[C:29]([S:42][C:10]2[C:11](=[O:13])[O:12][C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:8][C:9]=2[OH:14])=[CH:30][C:31]([CH3:41])=[C:32]([O:34][S:35](=[O:39])(=[O:40])[NH:36][CH2:37][CH3:38])[CH:33]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10551814toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) esterHCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 54689051N-Ethylsulfamic acid, 5-tert-butyl-4-{6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 from 6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (156 mg, 0.499 mmol; prepared in Example NN), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example VVV; 250 mg, 0.546 mmol), K2CO3 (303 mg, 2.195 mmol), and DMF (4 mL). The reaction was stirred at room temperature for 2.5 hours and then worked up in the usual manner. The crude product was flash chromatographed using CH2Cl2 :MeOH (98:2 to 97:3) to give the desired product as a amorphous solid. 1H NMR (CDCl3) δ 1.0-2.1 (m, 16 H), 1.55 (s, 9 H), 2.00 (s, 3 H), 2.6-2.7 (m, 3 H), 3.10 (d, 1 H), 3.3-3.4 (m,2 H), 4.96 (t, 1 H), 6.70-6.78 (d, s, 3 H), 6.93 (d, 2 H), 7.29 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customchromatographed

Sources & evidence

ORD record
ord-70afe20081e54fb08869049178bda7c9
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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