Lithium Hydroxide → HCID 11478488, compound

HRID 2216515Notes

Reaction equation

HRID 2216515 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]=[C:36](\[CH3:42])/[C:37]([O:39]CC)=[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]=[C:36](\[CH3:42])/[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 11238631HCID 11238631, compound

Product 1

HCID 11478488HCID 11478488, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl ester 4.4 (55 mg, 0.094 mmol) was stirred with 1N LiOH (1 ml) in 4 ml of MeOH/THF (1:3) at rt for 24 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). Concentration gave a crude product which was purified by semi-preparative HPLC (gradient elution: 70 to 100% CH3CN/H2O+0.1% TFA) to give 4.5,47 mg (90%). HRMS (ESI) calc'd for C33H34ClN2O4 577.2207, found 557.2218 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=1.1, 1H), 7.39–7.25 (m, 7H), 7.19 (d, J=2.5, 1H), 7.00–6.95 (m, 3H), 6.47 (s, 1H), 4.95 (s, 2H), 4.14–4.05 (m, 1H), 3.88 (s, 3H), 2.24 (s, 3H), 2.10–1.98 (m, 2H), 1.94–1.87 (m, 4H), 1.27–1.22 (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. concentrationConcentration

Sources & evidence

ORD record
ord-051ef6860ec74b1bbd81f5e561627755
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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