Potassium Carbonate → HCID 54688364, compound

HRID 356562Notes

Reaction equation

HRID 356562 reaction equation
[OH:1][C:2]1[CH2:7][C@@:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=[O:20])[CH:3]=1.[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([S:29]S(C2C=CC(C)=CC=2)(=O)=O)=[C:24]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([S:29][C:3]2[C:4](=[O:20])[O:5][C:6]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH:8]([CH3:10])[CH3:9])[CH2:7][C:2]=2[OH:1])=[C:24]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10569823Toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) esterHCID 54682331(S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Product 1

HCID 54688364HCID 54688364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 using 3.0 g (10.86 mmol) of (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (prepared in Example WWWW), 3.98 g (11.40 mmol) of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester (prepared in Example HHHH), 4.50 g of anhydrous K2CO3 and 54 mL DMF. The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated. The crude material was purified by flash silica gel chromatography, eluting with EtOAc, to give the title compound, m.p. 147°-149° C. (dec.). 1H-NMR (DMSO-d6) δ 0.89 (d, 3 H), 0.93 (d, 3 H), 1.42 (s, 9 H), 1.71 (s. 3 H), 1.85-1.93 (m, 2 H), 2.15 (m, 1 H), 2.41-2.50 (m, 2 H, partially obscured by DMSO), 2.67 (d of ABX q, 1 H), 2.89 (d of ABX q, 1 H), 6.55 (s, 1 H), 6.60 (s, 1 H), 6.64 (d, 2H), 6.93 (d, 2H), 9.13 (br s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customThe reaction was quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by flash silica gel chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-c4619de1b1ad4028b0623f9b40a7541e
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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