Diethyl Ether → HCID 86623033, compound

HRID 1359978Notes

Reaction equation

HRID 1359978 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[CH3:13][CH:14]([C:28]([OH:30])=[O:29])[C:15]1[CH:16]=[CH:17][C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:19]([F:21])[CH:20]=1.[ClH:31].C(OCC)(=O)C.C(OCC)C>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[CH3:13][CH:14]([C:28]([OH:30])=[O:29])[C:15]1[CH:16]=[CH:17][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:19]([F:21])[CH:20]=1.[ClH:31]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623032HCID 86623032, compound2×

Product 1

HCID 86623033HCID 86623033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 ml of dichloromethane, 720 mg (1.79 mmol) of the Boc-aminopropanol-flurbiprofen obtained above was dissolved, and 4 ml of 4 M hydrochloric acid/ethyl acetate was added thereto under ice-cooling, followed by stirring under ice-cooling for 3 minutes and at room temperature for 3 hours and 10 minutes. After confirming disappearance of Boc-aminopropanol-flurbiprofen by TLC, diethyl ether was added thereto, followed by decantation twice. Thereafter, the residue was dried under reduced pressure to give the titled substance at a yield of 352 mg (94%). 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 give the titled substance at a yield of 352 mg (94%)

Sources & evidence

ORD record
ord-0c2c188223ad4852a4239a7b4a50bbd8
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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