Lithium Hydroxide → HCID 11753092, compound

HRID 2216512Notes

Reaction equation

HRID 2216512 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[N:27]=[C:26](/[CH:35]=[CH:36]/[C:37]([O:39]C)=[O:38])[CH:25]=3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[Li+].[OH-]>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[N:27]=[C:26](/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38])[CH:25]=3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11284352HCID 11284352, compound

Product 1

HCID 11753092HCID 11753092, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl ester 3.2 (40 mg) and 1N LiOH (1 ml) in 3 ml MeOH/THF (1:2) was stirred at rt 18 h before being concentrated and partitioned between EtOAc and H2O. The aqueous layer was acidified with 1N HCl and extracted with EtOAc (3×). The organic extracts were washed with H2O, brine, and dried (Na2SO4). Concentration gave 3.3, 39 mg (100%). HRMS (ESI) calc'd for C32H32ClN2O4 542.1972; found 543.2050 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=15.8, 1H), 7.39–7.23 (m, 7H), 7.18 (d, J=2.6, 1H), 6.99–6.94 (m, 3H), 6.45 (s, 1H), 6.38 (d, J=6.1, 1H), 4.94 (s, 2H), 4.13–4.01 (m, 1H), 3.88 (s, 3H), 2.04–1.83 (m, 6H), 1.32–1.21 (m, 4H).

Workup

  1. concentrationbefore being concentrated
  2. custompartitioned between EtOAc and H2O
  3. extractionextracted with EtOAc (3×)
  4. washThe organic extracts were washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration
  7. customgave 3.3, 39 mg (100%)

Sources & evidence

ORD record
ord-94a6b55c626d4acba9461c8ecec57c5d
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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