Diethyl Ether → HCID 86623037, compound

HRID 1359984Notes

Reaction equation

HRID 1359984 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[CH:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:24]=2)=[CH:17][CH:18]=1.C(OC(=O)C)C.[ClH:38].C(OCC)C>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[CH:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.[ClH:38]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623036HCID 86623036, compound2×

Product 1

HCID 86623037HCID 86623037, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Boc-aminopropanol-fenbufen obtained above (1.82 mmol) was dissolved in dichloromethane (4 ml), and under ice-cooling, 4 N hydrochloric acid ethyl acetate solution (4 ml) was added thereto, and then the mixture was gradually returned to room temperature and stirred for 90 minutes. Precipitation of white precipitate was observed just after the commencement of the reaction. After confirming disappearance of Boc-aminopropanol-fenbufen by TLC, diethyl ether was added to the reaction solution, and the resulting white precipitate was centrifuged. The precipitate was washed three times with diethyl ether and then dried under reduced pressure to give the titled compound (621.4 mg, yield 98%). The structure was identified by 1H-NMR (CDCl3:CD3OD=1:1).

Workup

  1. temperatureunder ice-cooling
  2. customwas gradually returned to room temperature
  3. customPrecipitation of white precipitate
  4. customafter the commencement of the reaction
  5. additionwas added to the reaction solution
  6. washThe precipitate was washed three times with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f09339abd3534153b51f036dc0ab3aa8
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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