Diethyl Ether → HCID 86623042, compound

HRID 1359989Notes

Reaction equation

HRID 1359989 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[CH3:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]3[CH2:24][CH2:25][O:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])([CH2:28][CH3:29])[C:22]=3[NH:21][C:20]=12.[ClH:34].C(OCC)(=O)C.C(OCC)C.CCCCCC>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[CH3:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]3[CH2:24][CH2:25][O:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])([CH2:28][CH3:29])[C:22]=3[NH:21][C:20]=12.[ClH:34]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623041HCID 86623041, compound

Product 1

HCID 86623042HCID 86623042, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 ml of dichloromethane, 421.5 mg (0.948 mmol) of the Boc-aminopropanol-etodolac obtained above was dissolved, and 3 ml of 4 M hydrochloric acid/ethyl acetate was added thereto under ice-cooling, followed by stirring for 3 hours. Diethyl ether and hexane were added thereto for precipitation, and the precipitate was dried under reduced pressure. The precipitate was purified by silica gel column chromatography to give 197.6 mg (55%) of the titled compound. The structure was identified by 1H-NMR.

Workup

  1. dissolutionabove was dissolved
  2. temperatureunder ice-cooling
  3. customfor precipitation
  4. customthe precipitate was dried under reduced pressure
  5. customThe precipitate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a55a660442f646f39dea9282dacaa94a
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

Loading…