Lithium Hydroxide → HCID 11211862, compound

HRID 2216517Notes

Reaction equation

HRID 2216517 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]([CH2:26][CH2:27][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-]>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]([CH2:26][CH2:27][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 11258624HCID 11258624, compound

Product 1

HCID 11211862HCID 11211862, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl ester 6.1 (53 mg) was stirred with 1N LiOH (2 ml) in 5 ml of MeOH/THF (4:1) over 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 organic extracts were washed with H2O, brine, and dried (Na2SO4). The residue after concentration was triturated with hexanes/Et2O (10:1) to afford acid 6.2, 39 mg (100%). HRMS (ESI) calc'd for C25H29N2O3 405.2100, found 405.2198 (MH+); MS (ESI); 1H NMR (300 MHz, CDCl3) δ 7.48–7.34 (m, 5H), 7.27 (d, J=7.0, 2H), 7.06 (d, J=8.7, 2H), 6.01 (s, 1H), 5.13 (s, 2H), 4.06–3.98 (m, 1H), 3.02–2.97 (m, 2H), 2.85–2.81 (m, 2H), 1.91–1.83 (m, 6H), 1.26 (br s, 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 organic extracts were washed with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationThe residue after concentration
  8. customwas triturated with hexanes/Et2O (10:1)
  9. customto afford acid 6.2, 39 mg (100%)

Sources & evidence

ORD record
ord-ffc981e197e149bf8d10ab7600a75f75
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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