Water → HCID 86623026, compound

HRID 1359971Notes

Reaction equation

HRID 1359971 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:31]=[CH:30][CH:29]=[C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])[CH:19]=1)[CH3:17])=[O:15].O>ClCCl.CN(C)C1C=CN=CC=1>[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:31]=[CH:30][CH:29]=[C:20]([C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:22])[CH:19]=1)[CH3:17])=[O:13]

Participants

6

Reactant 3

HCID 962WaterHCID 3825KetoprofenHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623026HCID 86623026, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 14 ml of dichloromethane, 2.371 g (13.5 mmol) of Boc-aminopropanol and 3.441 g (13.5 mmol) of ketoprofen (manufactured by Tokyo Kasei Kogyo) were dissolved, and 323 mg (2.6 mmol) of 4-dimethylaminopyridine (DMAP) and 2.833 g (14.8 mmol) of water-soluble carbodiimide hydrochloride (WSCI.HCl)/14 ml dichloromethane were added thereto in this order under ice-cooling. After returning to room temperature and stirring overnight, 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 5.430 g of the titled compound (yield 98%). 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-446d44b04eba4304ba30c14588ce337b
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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