Diethyl Ether → HCID 86623031, compound

HRID 1359976Notes

Reaction equation

HRID 1359976 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[OH:13][C:14]([CH:16]([C:18]1[CH:27]=[CH:26][C:21]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:20][CH:19]=1)[CH3:17])=[O:15].[ClH:28].C(OCC)(=O)C.C(OCC)C>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[ClH:28].[OH:15][C:14]([CH:16]([C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH:23]([CH3:24])[CH3:25])=[CH:26][CH:27]=1)[CH3:17])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623030HCID 86623030, compound2×

Product 1

HCID 86623031HCID 86623031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 ml of dichloromethane, 636 mg (1.75 mmol) of the Boc-aminopropanol-ibuprofen 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 10 minutes and at room temperature for 3 hours. After confirming disappearance of Boc-aminopropanol-ibuprofen by TLC, diethyl ether was added thereto, followed by decantation three times. Thereafter, the residue was dried under reduced pressure to give the titled substance at a yield of 406 mg (77%). 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 406 mg (77%)

Sources & evidence

ORD record
ord-7ee59dc42ab54a91945caeae2f1026ab
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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