Ibuprofen, (+-)- → HCID 86623030, compound

HRID 1359975Notes

Reaction equation

HRID 1359975 reaction equation
[C:1]([O:5][C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[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].CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>ClCCl.CN(C1C=CN=CC=1)C>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[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

7

Reactant 4

HCID 3672Ibuprofen, (+-)-HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623030HCID 86623030, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 2 ml of dichloromethane, 352 mg (2 mmol) of Boc-aminopropanol and 412 g (2 mmol) of ibuprofen (manufactured by Wako Pure Chemical Industries) were dissolved, and 48 mg (0.4 mmol) of DMAP and 423 g (2.2 mmol) of WSCI.HCl/2 ml dichloromethane were added thereto in this order under ice-cooling. After returning to room temperature and stirring overnight, and ethyl acetate was added thereto, followed by separation by washing with 5% citric acid twice, water, 5% sodium hydrogen carbonate twice, water and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure to give 665 mg of the titled compound (yield 91%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperaturein this order under ice-cooling
  2. customAfter returning to room temperature
  3. customfollowed by separation
  4. washby washing with 5% citric acid twice
  5. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-a16c3de52f6a42cdae7ac3997c27876b
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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