Sodium borohydride → HCID 86592484, compound

HRID 460024Notes

Reaction equation

HRID 460024 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:34])[CH2:16][CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[CH3:33])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[BH4-].[Na+]>O1CCCC1.O>[OH:34][CH:15]([C:13]1[CH:12]=[CH:11][C:3]([O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]([CH3:1])[CH:14]=1)[CH2:16][CH2:17][C:18]1[S:22][C:21]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=2)=[N:20][C:19]=1[CH3:33]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58824789HCID 58824789, compound

Product 1

HCID 86592484HCID 86592484, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl [2-methyl-4-(3-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}propanoyl)phenoxy]acetate (intermediate11, 0.28 g) in tetrahydrofuran (8 ml) and water (8 ml) at 0° C. was treated portion-wise with sodium borohydride (0.043 g) and the mixture was stirred at 0° C. for 1 hour. The solvent was evaporated and the residue partitioned between water and ethyl acetate; the aqueous layer was separated and extracted twice more with ethyl acetate. The combined organic solutions were dried with brine and over magnesium sulfate and concentrated. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (3:1) as eluent to give the title compound as a colourless gum.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between water and ethyl acetate
  3. customthe aqueous layer was separated
  4. extractionextracted twice more with ethyl acetate
  5. dry with materialThe combined organic solutions were dried with brine and over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product isolated
  8. customafter evaporation of the solvent
  9. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-12d38a5839a548ea9d5d7c4b43366b39
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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