Potassium Carbonate → HCID 178429697, compound

HRID 1003900Notes

Reaction equation

HRID 1003900 reaction equation
[OH:1][C:2]1[CH2:7][C@@:6]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:22])[CH:3]=1.C([C:27]1[CH:32]=[C:31]([CH2:33][OH:34])[C:30]([CH3:35])=[CH:29][C:28]=1[S:36]S(C1C=CC(C)=CC=1)(=O)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:6]([SH:36]([C:28]1[CH:29]=[C:30]([CH3:35])[C:31]([CH2:33][OH:34])=[CH:32][CH:27]=1)[C:3]1[C:4](=[O:22])[O:5][C:6]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][C:2]=1[OH:1])([CH3:14])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 70253612HCID 70253612, compound

Product 1

HCID 178429697HCID 178429697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 using 0.12 g (0.40 mmol) of (S)-4-hydroxy-6-phenethyl-6-phenyl-5,6-dihydro-pyran-2-one (prepared in Example VV), 0.16 g (0.44 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF), 0.22 g (1.6 mmol) of K2CO3, and DMF (2 mL). Upon standard work-up, the residue was chromatographed on silica gel, eluting with 4:1 CHCl3 :EtOAc, to give the title compound, m.p. 186-187° C. 1H NMR (DMSO-d6) δ (s, 9 H), 1.75 (s, 3 H), 2.25 (m, 3 H), 2.55 (m, 1 H), 3.51 (q, partially obscured by H2O, 2 H), 4.32 (br s , 2 H), 4.90 (br s , 1 H), 6.17 (s, 1 H), 7.09 (m, 2 H), 7.15 (m, 1 H), 7.23 (m, 3 H), 7.37 (m, 1 H), 7.44 (m, 4 H).

Workup

  1. customThe title compound was prepared
  2. customUpon standard work-up, the residue was chromatographed on silica gel
  3. washeluting with 4:1 CHCl3

Sources & evidence

ORD record
ord-c992fc0e472445c6a1670876e3277016
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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