Diethyl Ether → HCID 86623029, compound

HRID 1359974Notes

Reaction equation

HRID 1359974 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[CH3:13][C@H:14]([C:27]([OH:29])=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.[ClH:30].C(OCC)(=O)C.C(OCC)C>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[CH3:13][C@H:14]([C:27]([OH:29])=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.[ClH:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623028HCID 86623028, compound2×

Product 1

HCID 86623029HCID 86623029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 ml of dichloromethane, 684 mg (1.76 mmol) of the Boc-aminopropanol-naproxen obtained above was dissolved, and 2 ml of 4 M hydrochloric acid/ethyl acetate was added thereto under ice-cooling, followed by stirring under ice-cooling for 20 minutes and at room temperature for 1 hour. After confirming disappearance of Boc-aminopropanol-naproxen by TLC, and diethyl ether was added thereto, followed by decantation three times. Thereafter, the residue was dried under reduced pressure to quantitatively give the titled substance at a yield of 564 mg. The structure was identified by 1H-NMR (CDCl3).

Workup

  1. dissolutionabove was dissolved
  2. temperatureunder ice-cooling
  3. additionwas added
  4. customThereafter, the residue was dried under reduced pressure
  5. customto quantitatively give the titled substance at a yield of 564 mg

Sources & evidence

ORD record
ord-ea6b9a5f2cb84617b21ee1850d62e6f5
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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