Hydrochloric Acid → HCID 59402655, compound

HRID 538530Notes

Reaction equation

HRID 538530 reaction equation
C([O-])([O-])=O.[K+].[K+].C([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([NH2:27])=[O:26])[CH:20]=2)[CH:12]=1)(=O)C.Cl.CCOCC>O>[OH:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH2:17][O:18][C:19]1[CH:20]=[C:21]([C:25]([NH2:27])=[O:26])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 59402667HCID 59402667, compound

Product 1

HCID 59402655HCID 59402655, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of K2CO3 (500 mg, 3.62 mmol, 5.75 equiv.) in water (5 ml) was added to a solution of 3-[3-(aminocarbonyl)phenoxy]methylphenyl acetate (180 mg, 0.63 mmol, 1 equiv.) and the mixture was stirred at r.t., under N2, for 3 h; The mixture was acidified with 10% HCl solution to pH 1, and was extracted with EtOAc (2×30 ml). The combined organic extracts were washed with water (30 ml), dried (Na2SO4) and evaporated to dryness under reduced pressure, to give a clear oil residue which, after trituration with Et2O, solidified to a white solid (70 mg, 46% yield). Mp 122-123° C., HPLC-MS (method 1): m/z 244 [M+H]+. Rt=2.92 min.

Workup

  1. extractionwas extracted with EtOAc (2×30 ml)
  2. washThe combined organic extracts were washed with water (30 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness under reduced pressure
  5. customto give a clear oil residue which

Sources & evidence

ORD record
ord-dff601702d114ee8a68b96d9c151cb83
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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