Naproxen → HCID 86623028, compound

HRID 1359973Notes

Reaction equation

HRID 1359973 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][C@H:14]([C:27]([OH:29])=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.CCN=C=NCCCN(C)C.Cl>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][C@H:14]([C:27]([OH:29])=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1

Participants

6

Reactant 3

HCID 156391NaproxenHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623028HCID 86623028, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In 2 ml of dichloromethane, 350 mg (2 mmol) of Boc-aminopropanol and 462 g (2 mmol) of naproxen (manufactured by Wako Pure Chemical Industries) were dissolved, and 48 mg (0.4 mmol) of DMAP and 422 g of WSCI.HCl (2.2 mmol)/2 ml dichloromethane were added thereto in this order under ice-cooling. After returning to room temperature and stirring for 4 hours and 50 minutes, dichloromethane was evaporated under reduced pressure, 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 720 mg of white crystal of the titled compound (yield 93%). The structure was identified by 1H-NMR (CDCl3).

Workup

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

Sources & evidence

ORD record
ord-cdbddf48db174fdcbc30ba1ef0e14710
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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