Sodium Hydroxide → HCID 22261224, compound

HRID 898488Notes

Reaction equation

HRID 898488 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 bottom flask were charged 0.10 g (0.17 mmol) of 3-{2-cyclohexylcarbamoyloxymethyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid ethyl ester dissolved in 2 mL of ethanol. Next this solution was treated with 0.48 mL (0.96 mmol) of 2N NaOH and then heated to 55° C. for 2 h. The volatiles were removed in vacuo and this crude residue was taken up in 20 mL of EtOAc and 10 mL brine and acidified with 1 mL of 5N HCl. The aqueous layer was discarded and the organic layer was dried over Na2SO4 and removed in vacuo. 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. customThe volatiles were removed in vacuo
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customremoved in vacuo
  4. customThe crude residue was submitted for mass-directed HPLC purification

Sources & evidence

ORD record
ord-ed2cad8464ec427eb46774bd10f5af1b
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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