Sodium Hydroxide → HCID 22261224, compound

HRID 1181140Notes

Reaction equation

HRID 1181140 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:19][CH:20]=2)=[CH:9][C:8]=1[CH2:27][O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)C.[OH-].[Na+]>C(O)C>[CH:31]1([NH:30][C:29]([O:28][CH2:27][C:8]2[CH:9]=[C:10]([O:13][CH2:14][CH2:15][C:16]3[N:17]=[C:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[O:19][CH:20]=3)[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]([OH:38])=[O:3])=[O:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69232479HCID 69232479, compound

Product 1

HCID 22261224HCID 22261224, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a 15 mL round bottomed flask was charged with 3-{2-cyclohexylcarbamoyloxymethyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid ethyl ester (0.10 g, 0.17 mmol), ethanol (2 mL), and then 2N NaOH (0.48 mL, 0.96 mmol). The solution was heated at 55° C. for 2 h. The mixture was concentrated, acidified using 5% H2SO4 (1.5 mL), and partitioned between CH2Cl2 (15 mL) and brine (15 mL). The organic layer was dried (Na2SO4), filtered, and concentrated and was concentrated. The crude residue was submitted for mass-directed HPLC purification to give a white solid (0.058 g, 63%). MS (ES) m/e 537 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between CH2Cl2 (15 mL) and brine (15 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationwas concentrated
  7. customThe crude residue was submitted for mass-directed HPLC purification

Sources & evidence

ORD record
ord-7332ca513a4f4f169a5d6137780c7304
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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