Lithium Hydroxide → HCID 69129073, compound

HRID 749031Notes

Reaction equation

HRID 749031 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=1.[OH-].[Li+]>C1COCC1.O>[C:30]([O:29][C:27]([NH:26][CH:20]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:14][CH:15]=1)=[O:28])([CH3:32])([CH3:31])[CH3:33]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69108521HCID 69108521, compound

Product 1

HCID 69129073HCID 69129073, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester 61 (0.8 g, 1.65 mmol) was dissolved in THF (10 mL) and diluted with water (10 mL). Lithium hydroxide (0.158 g, 6.6 mmol) was added and the reaction mixture was stirred at room temperature for about 2 h. The THF was evaporated and the resulting aqueous layer was acidified with 2.0 M HCl and extracted into EtOAc (2×100 mL). The organic layer was washed with water (1×100 mL) and brine (1×100 mL), dried and concentrated to yield the desired acid compound 62 (0.7 g, 97%). 1H NMR (400 MHz, DMSO-d6) 12.1 (s, 1H), 7.31 (dd, J=7.6 and 1.6 Hz, 1H) 7.21 (d, J=8.8 Hz, 2H), 7.18 (d, J=7.6 Hz, 1H), 7.08 (m, 2H), 6.82 (d, J=8.8 Hz, 2H), 6.76 (d, J=8.0 Hz, 1H), 4.52 (m, 1H), 2.88-2.81 (m, 10H), 1.31 (s, 9H)

Workup

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×100 mL)
  3. washThe organic layer was washed with water (1×100 mL) and brine (1×100 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19fe2153ab7746d48bba9230b7a0e807
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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