Sodium Hydroxide → HCID 11568313, compound

HRID 1442684Notes

Reaction equation

HRID 1442684 reaction equation
C[O:2][C:3]([C:5]1[CH:33]=[CH:32][C:8]2[N:9]=[C:10]([C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[C:19]([CH3:31])[CH:18]=3)([CH2:15][CH3:16])[CH2:13][CH3:14])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[CH3:29][C:26]([CH3:27])([CH3:28])[C:25](=[O:30])[CH2:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]([C:10]2[O:11][C:7]3[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:33]=[CH:32][C:8]=3[N:9]=2)([CH2:13][CH3:14])[CH2:15][CH3:16])=[CH:18][C:19]=1[CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59166708HCID 59166708, compound

Product 1

HCID 11568313HCID 11568313, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzooxazole-6-carboxylic acid methyl ester (1.50 g, 3.32 mmol) in MeOH (10 mL) and THF (10 mL) is treated with NaOH (2.0 M, 20.0 mL). The resulting mixture is stirred at RT for 16 h. The mixture is concentrated, acidified with HCl (5 N) until pH˜3, and extracted with EtOAc (100 mL, then 50 mL). The organic layer is dried over Na2SO4, filtered, and concentrated to afford the title compound (1.40 g, 97%). H-NMR (ppm, CDCl3) δ: 8.16 (1H, d, J=1.3 Hz), 8.11 (1H, dd, J=1.3, 8.4 Hz), 7.78 (1H, d, J=8.4 Hz), 7.02 (1H, d, J=1.8 Hz), 6.97 (1H, dd, J=2.2, 8.4 Hz), 6.54 (1H, d, J=8.4 Hz), 4.85 (2H, s), 2.40 (2H, q, J=7.5 Hz), 2.30 (2H, q, J=7.5 Hz), 2.26 (3H, s), 1.25 (9H, s), 0.77 (6H, t, J=7.5 Hz). MS (ES) m/e: 438.2 (M+1), 436.2 (M−1).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (100 mL
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-970df14700ac40369948140bb3a44ea7
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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