Lithium Hydroxide → 3-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid

HRID 748978Notes

Reaction equation

HRID 748978 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[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]=2)=[CH:8][CH:7]=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:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:7][CH:8]=2)=[CH:14][CH:15]=1)=[O:28])([CH3:32])([CH3:31])[CH3:33]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59762818HCID 59762818, compound

Product 1

HCID 597628113-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acidYield 103.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Amide 5 (8.4 g, 17.0 mmol) was dissolved in THF (60 mL) and diluted with water (60 mL). Lithium hydroxide (1.66 g, 69.0 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 6 (8.0 g, 97%). 1H NMR (400 MHz, DMSO-d6): 12.15 (br, 1H), 7.22 (overlapped d, J=8.4 Hz, 4H), 7.06 (d, J=8.4 Hz, 1H), 6.88 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.53 (m, 1H), 2.91 (s, 3H), 2.73-2.83) (m, 9H), 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-4da061695679419fb2d8ea42faa8ea43
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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