Sodium Hydroxide → HCID 67544979, compound

HRID 386437Notes

Reaction equation

HRID 386437 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.O.CO>[C:1]([O:5][C:6]([N:8]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67544145HCID 67544145, compound

Product 1

HCID 67544979HCID 67544979, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl 3-(4-(tert-butoxycarbonyl(phenyl)amino)phenyl)propanoate (S34), 390 mg, 1.10 mmol) in a mixture of THF/H2O/MeOH (3/1/0.4, 4 mL), was treated with NaOH (100 mg, 2.5 mmol) and was stirred for 4 h at 25° C. The reaction mixture was concentrated, diluted with aqueous 1 N HCl and extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to afford S35 (370 mg, 1.08 mmol, 99%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) 7.34-7.29 (m, 2H), 7.23-7.15 (m, 7H), 2.94 (t, 2H, J=7.6 Hz), 2.66 (t, 2H, J=7.6 Hz), 1.46 (s, 9H); 13C NMR (CDCl3, 100 MHz) 178.7, 153.9, 142.9, 141.2, 137.6, 128.6, 128.5, 126.9 (2C), 125.6, 81.1, 35.5, 30.0, 28.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with aqueous 1 N HCl
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford S35 (370 mg, 1.08 mmol, 99%) as a yellow oil

Sources & evidence

ORD record
ord-80e893ffb8174401a9e8381fe31fb8d5
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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