Hydrochloric Acid → HCID 54682295, compound

HRID 1003913Notes

Reaction equation

HRID 1003913 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[S:12][C:13]1[C:18](=[O:19])[O:17][C:16]([C:28]2[CH:41]=[CH:40][C:31]([O:32][CH2:33][CH2:34]OS(C)(=O)=O)=[CH:30][CH:29]=2)([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][C:14]=1[OH:42])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.Cl>CN(C=O)C.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[S:12][C:13]1[C:18](=[O:19])[O:17][C:16]([C:28]2[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[CH:40][CH:41]=2)([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:15][C:14]=1[OH:42])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86753331HCID 86753331, compound

Product 1

HCID 54682295HCID 54682295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by combining methanesulfonic acid 2-{4-[5-(2-tert-butyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-oxo-2-phenethyl-3,6-dihydro-2H-pyran-2-yl]-phenoxy} -ethyl ester (0.07 g, 0.1 15 mmol) from the previous paragraph, K2CO3 (0.08 g, 0.57 mmol), and morpholine (0.15 mL, 1.72 mmol) in DMF (2 mL). The reaction was stirred overnight at room temperature then combined with H2O and acidified to pH 6.0 with 1N HCl. The product was extracted with EtOAc, dried (MgSO4) and concentrated. Purification by silica gel chromatography, eluting with MeOH:CH2Cl2 :hexane (1:50:50) gave the title compound, m.p. 140-150° C. 1H NMR (CDCl3) δ 1.48 (s, 9 H), 1.80 (s, 3 H), 2.17-2.29 (m, 3 H), 2.38 (m, 1 H), 2.63 (m, 4 H), 2.84 (m, 2 H), 3.21 (dd, 2 H), 3.74 (m, 4 H), 4.00 (m, 2 H), 6.15 (s, 1 H), 6.78 (m, 2 H), 7.05 (d, 2 H), 7.10-7.22 (m, 5 H), 7.32 (d, 2 H).

Workup

  1. customThe title compound was prepared
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography
  6. washeluting with MeOH:CH2Cl2 :hexane (1:50:50)

Sources & evidence

ORD record
ord-ffabfa11f4174b238867d13e03c3c425
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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