Lithium Hydroxide → 3-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid

HRID 749004Notes

Reaction equation

HRID 749004 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:20](=[O:24])[N:21]([CH3:23])[CH3:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[C:29]([O:28][C:26]([NH:25][CH:19]([C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[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:33])=[O:2])=[CH:7][CH:8]=2)=[CH:14][CH:15]=1)=[O:27])([CH3:31])([CH3:30])[CH3:32]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 597511213-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 597511203-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Amide 32 (3.6 g, 7.9 mmol) was dissolved in THF (40 mL) and diluted with water (40 mL). Lithium hydroxide (0.76 g, 31.0 mmol) was added and the reaction mixture was stirred at room temp 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 (1×150 mL) and brine (1×200 mL), dried and concentrated to yield the desired acid compound 33 (3.4 g, 97%). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 7.34 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.0 Hz, 1H), 6.93 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 5.50 (d, J=8.0 Hz, 1H), 2.90 (s, 3H), 2.84 (s, 3H), 2.81 (t, J=7.6 Hz, 2H), 2.53 (t, J=7.6 Hz, 2H), 1.37 (s, 9H).

Workup

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×100 mL)
  3. washThe organic layer was washed with water (1×150 mL) and brine (1×200 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3e5cbdc1ebae4debb15ca1582c418f88
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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