Methanesulfonic Acid → HCID 58954443, compound

HRID 1535052Notes

Reaction equation

HRID 1535052 reaction equation
CS(O)(=O)=O.C(C1C(OC)=NC2C(C=1)=CC=C(SCCC[C:24]1[C:40](OCC3C=CC=CC=3)=[CH:39][C:27]3[CH2:28][CH:29]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:30][C:26]=3[CH:25]=1)C=2)(OC)=O.FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.C(OCC)C.O1CCCC1>[C:33]1([CH2:32][CH2:31][CH:29]2[CH2:28][C:27]3[CH:39]=[CH:40][CH:24]=[CH:25][C:26]=3[O:30]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 5

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 15161055HCID 15161055, compound

Product 1

HCID 58954443HCID 58954443, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Methanesulfonic acid (0.5 mL) was added dropwise to a solution of 6-[3-(carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E25, (1.1 gm; 1.7 mmoles), trifluoroacetic acid (11 mL) and thioanisole (3 mL) at 5° C. The mixture was stirred for 30 minutes and then added in portions to an ice cold stirring biphasic mixture of saturated sodium bicarbonate solution (150 mL), brine (25 mL), tetrahydrofurane (125 mL) and diethyl ether (25 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent to yield 900 mgs (95%) of 6-[3-(3-carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-hydroxy-2-(2-phenylethyl-2,3-dihydrobenzofuran, E26, that had crystallized from diethyl ether, m.p. 112°-114° C.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-5559acff13d54a05b08e46f0dc2eefbe
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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