Diethyl Ether → HCID 11188844, compound

HRID 2216510Notes

Reaction equation

HRID 2216510 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:18]=[C:17](/[CH:26]=[CH:27]/[C:28]([O:30]C)=[O:29])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].CCOCC>C1COCC1.CO>[CH:20]1([N:19]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][CH:11]=3)=[CH:16][C:17](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[N:18]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 11384502HCID 11384502, compound

Product 1

HCID 11188844HCID 11188844, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ester 2.3 (55 mg, 0.132 mmol) in 4.5 ml of THF/MeOH (8:1) was added 1N LiOH (2 ml), and the mixture was stirred for 24 h at rt. Concentration to remove solvent gave a residue that was taken Et2O and extracted with 0.1 N NaOH and H2O (2×). The combined aqueous extracts were acidified with concentrated HCl and extracted with EtOAc (3×). The combined organic extracts were washed with H2O, brine, dried (Na2SO4). The crude product was triturated with hexanes to afford 45.8 mg (86%) of acid 2.4. HRMS (ESI) calc'd for C25H27N2O3 403.1943; found 403.2019 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=16.1, 1H), 7.49–7.34 (m, 5H), 7.28 (d, J=8.8, 2H), 7.07 (d, J=8.8, 2H), 6.46 (s, 1H), 6.38 (d, J=15.7, 1H), 5.13 (s, 2H), 4.14–4.04 (m, 1H), 2.03–1.82 (m, 6H), 1.28–1.24 (m, 4H).

Workup

  1. concentrationConcentration
  2. customto remove solvent
  3. customgave a residue that
  4. extractionextracted with 0.1 N NaOH and H2O (2×)
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic extracts were washed with H2O, brine
  7. dry with materialdried (Na2SO4)
  8. customThe crude product was triturated with hexanes

Sources & evidence

ORD record
ord-7095ce2a749a45abbcfe9b73f5553718
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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