Diisopropylamine → HCID 53688597, compound

HRID 356537Notes

Reaction equation

HRID 356537 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH3:14].[CH2:24]([O:31][C:32](=[O:47])[NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42](=[O:46])[CH:43]([CH3:45])[CH3:44])=[CH:36][CH:35]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.O.CCOC(C)=O.C(O)(=O)C>[CH2:17]([O:16][C:13](=[O:15])[CH2:14][C:42]([CH2:41][CH2:40][C:37]1[CH:38]=[CH:39][C:34]([NH:33][C:32]([O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:47])=[CH:35][CH:36]=1)([OH:46])[CH:43]([CH3:44])[CH3:45])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 8785Benzyl acetateHCID 54438009HCID 54438009, compoundHCID 178418339Butyllithium

Product 1

HCID 53688597HCID 53688597, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 21.9 mL (156 mmol) of diisopropylamine in dry THF (100 mL) was cooled to -40° C. under nitrogen, treated dropwise with 125 mL of 1.2M n-BuLi (150 mmol), and stirred for 30 minutes. To this solution was added a solution of 22.5 g (150 mmol) of benzyl acetate in dry THF (70 mL). The mixture was stirred at -40° C. for 45 minutes and then treated with a solution of 16.2 g (50 mmol) of [4-(4-methyl-3-oxo-pentyl)-phenyl]-carbamic acid benzyl ester (prepared in Example HHHHH) at a rapid, dropwise rate. When addition was complete, the reaction mixture was stirred at -40° C. for 30 minutes. Acetic acid (50 mL) was added, and the mixture was warmed to room temperature. EtOAc and H2O were added. The organic layer was separated, washed with brine, and dried (MgSO4). Concentration gave a residue which was chromatographed on silica gel, eluting with EtOAc:hexane (40:60), to give the title compound. 1H NMR (CDCl3) δ 0.88-0.91 (t, 6 H), 1.65-1.75 (m, 2 H), 1.85-1.89 (m, 1 H), 2.46-2.61 (m, 4 H), 3.52 (s, 1 H), 5.11 (s, 2 H), 5.16 (s, 2 H), 6.55 (br s, 1 H), 7.02 (d, 2 H), 7.24-7.38 (m, 12 H).

Workup

  1. stirringThe mixture was stirred at -40° C. for 45 minutes
  2. additionWhen addition
  3. stirringthe reaction mixture was stirred at -40° C. for 30 minutes
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration
  8. customgave a residue which
  9. customwas chromatographed on silica gel
  10. washeluting with EtOAc:hexane (40:60)

Sources & evidence

ORD record
ord-8e76d077e95245e8a081680d1901c355
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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