Hydrochloric Acid → 2-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 456021Notes

Reaction equation

HRID 456021 reaction equation
[C:1]([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:32])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.Cl>C(O)C>[C:1]([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH:16]([OH:32])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 58451400HCID 58451400, compound

Product 1

HCID 584514012-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[(4-{[(4′-Fluorobiphenyl-4-yl)oxy]acetyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester 967 mg obtained in Example 2-1 was dissolved in ethanol (10 mL) and, under ice-cooling, sodium borohydride (75 mg) was added and the mixture was stirred for 2 hr 30 min. Water (10 mL) was added, pH was adjusted to about 3 with aqueous hydrochloric acid (1 mol/L), and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue purified by column chromatography (Moritex Corporation Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=9/1→6/4) to give the title compound as a pale-yellow oily substance (907 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue purified by column chromatography (Moritex Corporation Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=9/1→6/4)

Sources & evidence

ORD record
ord-aecaea652d9349b3b21b32acfd18ef99
Source dataset
uspto-grants-2013_07
Patent number
US08497382B2

Reaction notes

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