Water → HCID 86684752, compound

HRID 1408881Notes

Reaction equation

HRID 1408881 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([F:24])[C:7]([C:10]2([F:23])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH:2]=[CH2:3].[OH2:25].C([OH:30])(C)(C)C>>[OH:25][C@@H:2]([CH2:3][OH:30])[CH2:1][C:4]1[CH:5]=[C:6]([F:24])[C:7]([C:10]2([F:23])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]2)=[N:8][CH:9]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6386tert-ButanolHCID 68004032HCID 68004032, compound

Product 1

HCID 86684752HCID 86684752, compoundYield 97%

Procedure

To a solution of 24 (1.60 g, 4.7 mmol) in t-butanol (20 mL) and H2O (20 mL) AD-mix-beta (5.0 g) was added portion wise at 5° C. The reaction was slowly warmed to room temperature and further stirred at this temperature for 16 hrs. The reaction mixture was cooled down to 5° C. and then quenched by adding excess sodium sulfite and stirred for 20 min. The resulting mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×2). The organic layers were combined which was washed with brine, dried over Na2SO4, and concentrated. The obtained residue was and chromatographed on silica gel eluted with hexane/ethyl acetate (20%-100%) to afford 1.70 g (97%) of 25 as a colorless oil which was use directly for the next step. LC/Ms (M+1) 373.

Workup

  1. temperatureThe reaction mixture was cooled down to 5° C.
  2. customquenched
  3. additionby adding excess sodium sulfite
  4. stirringstirred for 20 min
  5. additionThe resulting mixture was diluted with water (100 mL)
  6. extractionextracted with ethyl acetate (100 mL×2)
  7. washwas washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on silica gel
  11. washeluted with hexane/ethyl acetate (20%-100%)

Sources & evidence

ORD record
ord-ffda992d10f6465fabebebe56085c085
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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