Tetrahydrofuran → 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

HRID 1884276Notes

Reaction equation

HRID 1884276 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]3[O:32][CH2:31]3)[C:25]([O:27]C)=[O:26])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.CCN(CC)CC.[SH:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>C1C=CC=CC=1.O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]([OH:32])[CH2:31][S:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoateHCID 178527881HCID 178527881, compound

Product 1

HCID 98919232-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-[2-oxo-5-(thiazol-2-yl)thio]methyl]-tetrahydrofuran: To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.7 g, 1.79 mmol) in benzene (5 mL) and Et3N (0.33 mL, 2.3 mmol) at room temperature is added slowly 2-mercaptothiazole (0.52 g, 4.48 mmol). The reaction mixture is stirred for 4 h at room temperature. The resulting mixture is diluted with water, and the mixture is then extracted three times with EtOAc. The combined EtOAc layer is consecutively washed with water, and brine, dried over MgSO4 and concentrated to an oil under reduced pressure. Purification is accomplished by column chromatography with hexane/EtOAc (4:1 to 7:3 to 6:4) eluent to give the desired product.

Workup

  1. extractionthe mixture is then extracted three times with EtOAc
  2. washThe combined EtOAc layer is consecutively washed with water, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-41a224d556ea4b4da3e5124b0273696d
Source dataset
uspto-grants-2004_07
Patent number
US06762198B2

Reaction notes

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