tert-Butyl acetate → HCID 91464311, compound

HRID 1818637Notes

Reaction equation

HRID 1818637 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].[C:19]([C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=3)[CH:30]=[C:29]2[C:38](OCC)=[O:39])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1>[C:19]([C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=3)[CH:30]=[C:29]2[C:38](=[O:39])[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 10908tert-Butyl acetateHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 67482349HCID 67482349, compound

Product 1

HCID 91464311HCID 91464311, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of LHMDS (36.5 mL, 1.0 M in THF, 36.5 mmol) was added tert-butyl acetate (4.92 mL, 36.5 mmol), dropwise. After 30 min, a solution of the title compound of Example 14 Step A (4.50 g, 12.2 mmol) in THF (12 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. NH4Cl and extracted twice with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20 to 100% EtOAc in hexanes) afforded the title compound: LCMS B, tr=3.11 min, m/z 462.2 [M+Na]+; 1H NMR (500 MHz, CDCl3) δ 7.69 (d, J=2.0 Hz, 1H), 7.31-7.24 (m, 5H), 6.97 (d, J=8.5 Hz, 2H), 5.80 (s, 2H), 3.85 (s, 2H), 1.39 (s, 9H), 1.25 (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 ethyl acetate
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (0 to 20%

Sources & evidence

ORD record
ord-3f9ca1038a6e445d831c49dd1480c83a
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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