Lithium Hydroxide → HCID 11429974, compound

HRID 2216513Notes

Reaction equation

HRID 2216513 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]=[C:27](\[CH3:33])/[C:28]([O:30]CC)=[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-]>CO.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][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]=[C:27](\[CH3:33])/[C:28]([OH:30])=[O:29])[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11155006HCID 11155006, compound

Product 1

HCID 11429974HCID 11429974, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl ester 4.1 (50 mg, 0.112 mmol) and 1N LiOH (2 ml) in 3 ml of MeOH/THF (1:2) was stirred at rt for 18 h, concentrated, and partitioned between Et2O and H2O. The organic phase was extracted with 0.1 N NaOH (2×), and the combined aqueous extracts were acidified with conc. HCl, and extracted with EtOAc (3×). The combined organic extracts were washed with H2O, brine, and dried (Na2SO4) before being concentrated to afford 47 mg (100%) of 4.2. HRMS (ESI) calc'd for C26H29N2O3 417.2178, found 417.2174 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=1.1, 1H), 7.49–7.36 (m, 5H), 7.30 (d, J=8.7, 2H), 7.07 (d, J=8.7, 2H), 6.45 (s, 1H), 5.14 (s, 2H), 4.14–4.07 (m, 1H), 2.26 (d, J=1.5, 3H), 2.07–2.00 (m, 2H), 1.95–1.84 (m, 4H), 1.36–1.22 (m, 4H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between Et2O and H2O
  3. extractionThe organic phase was extracted with 0.1 N NaOH (2×)
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-831d310f32e54a849f5b553a0b646a10
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

Loading…