Triphenylphosphine → 2-[(4-{2-[4-(Benzoylamino)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914296Notes

Reaction equation

HRID 914296 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][OH:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].O[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>O1CCCC1>[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:26]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 459327Benzamide, N-(4-hydroxyphenyl)-HCID 14357405DiethyldiazodicarboxylateHCID 597593522-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597592512-[(4-{2-[4-(Benzoylamino)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl esterYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (1.0 g) synthesized in Example 4 and N-(4-hydroxyphenyl)benzamide (703 mg) were dissolved in tetrahydrofuran (10 mL), triphenylphosphine (866 mg) and diethyl diazodicarboxylate (575 mg) were added thereto under ice-cooling, and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (1.1 g) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-90f2da2c87124d2e805a308c0f567c6a
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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