Formic Acid → HCID 11684746, compound

HRID 914447Notes

Reaction equation

HRID 914447 reaction equation
C([O:5][C:6](=[O:37])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])=[O:20])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.C(O)=O>O>[F:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[NH:21][C:19](=[O:20])[N:18]([CH2:17][CH2:16][C:14]1[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:37])=[O:5])[S:12][CH:13]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 59759406HCID 59759406, compound

Product 1

HCID 11684746HCID 11684746, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-[(4-{2-[3-(2,4-difluorophenyl)-1-heptylureido]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (0.67 g) obtained in Example 319-1 was added formic acid (10 mL), and the mixture was stirred at room temperature overnight, stirred at 50° C. for 3 hr and further stirred at 70° C. for 4 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (elution solvent hexane-ethyl acetate=1:1) to give the title compound (0.55 g) as a pale-brown oil.

Workup

  1. stirringstirred at 50° C. for 3 hr
  2. stirringfurther stirred at 70° C. for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (elution solvent hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1a24e289b6f646e2beb017913bc6b37e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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