Lithium Hydroxide → HCID 11327046, compound

HRID 2216520Notes

Reaction equation

HRID 2216520 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]([C:26]#[C:27][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]([C:26]#[C: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 11339380HCID 11339380, compound

Product 1

HCID 11327046HCID 11327046, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of ester 7.3 (68 mg, 0.157 mmol) and 1N LiOH (2 ml) in 6 ml MeOH/THF (1:2) was stirred 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) to afford 64 mg (100%) of acid 7.4. HRMS (ESI) calc'd for C25H25N2O3 401.1865, found 401.1855 (M+H+); 1H NMR (300 MHz, CDCl3) δ 7.48–7.37 (m, 5H), 7.26 (d, J=8.8, 2H), 7.08 (d, J=8.8, 2H), 6.51 (s, 1H), 5.13 (s, 2H), 4.15–4.06 (m, 1H), 2.05–1.97 (m, 2H), 1.90–1.87 (m, 4H), 1.28–1.23 (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)

Sources & evidence

ORD record
ord-670a0d8591f3417d8be2f76244571436
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

Loading…