tert-Butyl acetate → HCID 91509324, compound

HRID 1818635Notes

Reaction equation

HRID 1818635 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH3:12].[F:19][C:20]([F:47])([F:46])[O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=1)[C:26]([C:41](OCC)=[O:42])=[CH:25]2.C([O-])(O)=O.[Na+]>C1COCC1>[O:42]=[C:41]([C:26]1[N:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:33][CH:32]=2)[C:28]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:21][C:20]([F:19])([F:46])[F:47])=[CH:30][CH:29]=2)[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 10908tert-Butyl acetateHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 87416753HCID 87416753, compound

Product 1

HCID 91509324HCID 91509324, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) solution of LHMDS (4.5 mL, 1.0 M in THF, 4.5 mmol) in THF (13 mL) was added tert-butyl acetate (0.600 mL, 4.46 mmol), dropwise. After 30 min, a solution of the title compound of Example 13 Step A (620 mg, 1.50 mmol) in THF (4 mL) was added, and the mixture was held at −78° C. for 30 min, then was placed in a 0° C. bath. After 1.5 h, the reaction mixture was poured into sat. aq. NaHCO3 and extracted twice with EtOAc. The combined organic phases were concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% hexanes in EtOAc) afforded the title compound: LCMS B, tr=2.90 min, m/z 432.0 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.79 (d, J=8.5 Hz, 2H), 7.64 (s, 1H), 7.46 (s, 1H), 7.44 (d, J=8.5 Hz, 2H), 7.21 (dd, J=9.0, 2.0 Hz, 1H), 7.11 (d, J=9.0 Hz, 1H), 3.85 (s, 2H), 1.46 (s, 9H).

Workup

  1. waitthe mixture was held at −78° C. for 30 min
  2. customwas placed in a 0° C.
  3. waitAfter 1.5 h
  4. extractionextracted twice with EtOAc
  5. concentrationThe combined organic phases were concentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 30%

Sources & evidence

ORD record
ord-dcb5188314dc41cb982601a534ea500f
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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