Water → HCID 70652917, compound

HRID 1408878Notes

Reaction equation

HRID 1408878 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([F:23])[C:7]([N:10]2[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].[OH2:24].C([OH:29])(C)(C)C>>[OH:24][C@@H:2]([CH2:3][OH:29])[CH2:1][C:4]1[CH:5]=[C:6]([F:23])[C:7]([N:10]2[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

Participants

4

Reactant 3

HCID 962WaterHCID 6386tert-ButanolHCID 68003986HCID 68003986, compound

Product 1

HCID 70652917HCID 70652917, compoundYield 79%

Procedure

To a solution of 12 (1.60 g, 5.0 mmol) in t-butanol (40 mL) and H2O (40 mL) AD-mix beta (8.6 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, washed with brine, dried over Na2SO4, and concentrated. The obtained residue was chromatographed on silica gel eluted with hexane/ethyl acetate (20%-100%) to afford 1.40 g (79%) of 13 as a colorless oil. 1H NMR (CD3OD) 1.50 (9 H, s), 2.60 (1 H, dd, J=7.77, 14.00), 2.82 (1 H, dd, J=4.60, 14.48 Hz), 3.35 (4 H, m), 3.49 (2 H, m), 3.56 (4 H, m), 3.76 (1 H, m), 7.38 (1 H, dd, J=1.96, 13.80 Hz), 7.90 (1 H, m). LC/MS (M+1) 356.

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. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe obtained residue was chromatographed on silica gel
  11. washeluted with hexane/ethyl acetate (20%-100%)

Sources & evidence

ORD record
ord-fec822b6637048a48a98dab24837c576
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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