Sodium Hydroxide → 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid

HRID 479128Notes

Reaction equation

HRID 479128 reaction equation
C([O:3][C:4](=[O:47])[CH:5]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[C:39]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[NH:32][CH:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[C:4]([OH:47])=[O:3])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695571212-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Product 1

HCID 180034292-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.213 g (0.341 mmol) of 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 1.6 ml of THF/EtOH=1/1 and treated with 0.568 ml of 3N NaOH(5 eq). The reaction flask was stirred for 20 h at ambient temperature. The mixture was then poured onto crashed ice/NH4Cl, extracted twice with AcOEt, washed with brine, dried over sodium sulfate, and evaporated to dryness. Twofold crystallization from hexane/AcOEt yielded 0.199 g of the title product as yellow crystals of mp. 125° (dec.).

Workup

  1. additionThe mixture was then poured
  2. extractionextracted twice with AcOEt
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customTwofold crystallization from hexane/AcOEt

Sources & evidence

ORD record
ord-f2acfd50feca487c999732588a172213
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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