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

HRID 914505Notes

Reaction equation

HRID 914505 reaction equation
C([O:5][C:6](=[O:36])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][CH:23]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]3[C:24]2=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[CH:34]1[C:35]2[CH:23]([CH2:22][O:21][C:19]([NH:18][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:36])=[O:5])[S:12][CH:13]=3)=[O:20])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 597594012-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597590512-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acidYield 128.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (33 g) synthesized in Example 483-1 in dichloromethane (30 mL) was added trifluoroacetic acid (50 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. The solvent was concentrated under reduced pressure, and purified by silica gel chromatography (elution solvent; ethyl acetate) to give the title compound (38 g) as a pale-brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. custompurified by silica gel chromatography (elution solvent; ethyl acetate)

Sources & evidence

ORD record
ord-5d1b7865f9f9418383fef6969848d2af
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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