Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4,5-epoxypentanoate → 3-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-4-phenylmethoxy-5-[[(2-thiazolyl)thio]methyl]-tetrahydrofuran

HRID 413407Notes

Reaction equation

HRID 413407 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:25]3[O:27][CH2:26]3)[C:20]([O:22]C)=O)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1C=CC=CC=1.C(N(CC)CC)C.[SH:49][C:50]1[S:51][CH:52]=[CH:53][N:54]=1>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]3[CH:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:25]([CH2:26][S:49][C:50]4[S:51][CH:52]=[CH:53][N:54]=4)[O:27][C:20]3=[O:22])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 23508272Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4,5-epoxypentanoateHCID 23508724HCID 23508724, compoundHCID 178527881HCID 178527881, compound

Product 1

HCID 235082843-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-4-phenylmethoxy-5-[[(2-thiazolyl)thio]methyl]-tetrahydrofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-3-phenylmethoxy-4,5-epoxypentanoate 63e (285 mg, 0.558 mmol) is dissolved in benzene/triethylamine (2.5 mL, 0.101 mmol) and 2-mercaptothiazole (164 mg, 1.40 mmol) is added. The resulting mixture is then stirred at room temperature for four hours. The mixture is diluted with ethyl acetate and water and extracted with ethyl acetate (3 times). The organic layer is washed with water and brine, then dried over magnesium sulfate and concentrated to a clear oil. The crude material is adsorbed onto silica and purified over a silica column eluting with ethyl acetate/hexane (2/8) followed with ethyl acetate/hexane (1/1). Product fractions are combined and the solvent is removed in vacuo to give the desired product as a clear oil.

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a clear oil
  5. custompurified over a silica column
  6. washeluting with ethyl acetate/hexane (2/8)
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c35d71de901948fd8edf7a43f49ae1b7
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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