Sodium Hydroxide → HCID 18188099, compound

HRID 1357853Notes

Reaction equation

HRID 1357853 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[O:10][C:6]=2[CH:5]=[C:4]([CH2:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C@H:29]([CH3:36])[CH2:30][C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=2)=[O:21])[CH:3]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[O:10][C:6]=2[CH:5]=[C:4]([CH2:19][C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([CH:29]([CH3:36])[CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=2)=[O:21])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57226830HCID 57226830, compound

Product 1

HCID 18188099HCID 18188099, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl (R) 3-{4-[2-(4-methyl-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoate [0.14 g, Reference Example 15(a)] in methanol (2 mL) was treated with aqueous sodium hydroxide solution (1.2 mL, 1M) and then stirred at 50° C. for 2 hours. The mixture was diluted with water and partially evaporated. The residue was washed with diethyl ether and then acidified to pH 4. The precipitated solid was filtered and sucked dry to give the title compound (0.07 g) as a tan solid. LC-MS: RT=3.38 minutes (100% by ELSD); MS (ES+), 458 (MH+).

Workup

  1. custompartially evaporated
  2. washThe residue was washed with diethyl ether
  3. filtrationThe precipitated solid was filtered
  4. customsucked dry

Sources & evidence

ORD record
ord-a1a6c306d6114ae78a25e9091e032590
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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