Ethyl Acetate → 2-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

HRID 914504Notes

Reaction equation

HRID 914504 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][NH2:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:20]1[C:32]2[CH:31]([CH2:33][O:34][C:35](N3C(=O)CCC3=O)=[O:36])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>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][NH:18][C:35]([O:34][CH2:33][CH:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:32]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:36])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 108817731-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 9H-fluoren-9-ylmethyl esterHCID 597594492-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597594012-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[4-(2-aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (19 g) synthesized in Example 7 in tetrahydrofuran (60 mL) was added N-(9H-fluorene-9-ylmethyloxycarbonyl)succinimide (23 g), and the mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and saturated brine. The precipitate was filtered and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (33 g) as a pale-brown oil.

Workup

  1. washthe mixture was washed with water and saturated brine
  2. filtrationThe precipitate was filtered
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. custompurified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e54a07513fed49f9911356b691489a25
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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