Potassium Carbonate → 3-(4-Amino-2-tert-butyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

HRID 1003903Notes

Reaction equation

HRID 1003903 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[NH2:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31]([S:35]S(C2C=CC(C)=CC=2)(=O)=O)=[C:30]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31]([S:35][C:3]2[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[CH2:7][C:2]=2[OH:1])=[C:30]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10569823Toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) esterHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 546822773-(4-Amino-2-tert-butyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was synthesized following General Method 9 using 118 mg (0.33 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 150 mg (0.33 mmol) of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester (prepared in Example HHHH), 184 mg (1.32 mmol) of K2CO3 and 2 mL of DMF. The reaction was worked up by partitioning between EtOAc and H2O. The organic layer was separated and concentrated, then triturated with Et2O. The resultant solid was placed in chilled HCI-saturated CH2Cl2 and stirred for 18 hours. After concentration, the residue was triturated with Et2O to yield the title compound, m.p. 140-145° C. 1H NMR (DMSO-d6) δ 1.5 (s, 9 H), 1.9 (s, 3 H), 2.05 (m, 4 H), 2.5 (m, 6 H), 6.68 (d, 4 H), 6.75 (s, 1 H), 7.0 (d, 4 H), 7.35 (s, 1 H), 7.95 (s 2 H), 9.25 (s, 2 H).

Workup

  1. customThe compound was synthesized
  2. customby partitioning between EtOAc and H2O
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customtriturated with Et2O
  6. concentrationAfter concentration
  7. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-49d465f7b2704498a5e2909cbf1fb3d4
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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