Flurbiprofen → HCID 86623032, compound

HRID 1359977Notes

Reaction equation

HRID 1359977 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].[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.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].[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

Participants

7

Reactant 4

HCID 3394FlurbiprofenHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623032HCID 86623032, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 2 ml of dichloromethane, 352 mg (2 mmol) of Boc-aminopropanol and 489 g (2 mmol) of flurbiprofen (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, 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 753 mg of the titled compound (yield 94%). 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-086dc3146ad04293bcb3002b5d955634
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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