Diethyl Ether → Serinol ketoprofen Hydrochloride

HRID 1359993Notes

Reaction equation

HRID 1359993 reaction equation
C([NH:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])(OC(C)(C)C)=O.[OH:14][C:15]([CH:17]([C:19]1[CH:32]=[CH:31][CH:30]=[C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:20]=1)[CH3:18])=[O:16].[ClH:33].C(OCC)(=O)C.C(OCC)C.CCCCCC>ClCCl>[NH2:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11].[ClH:33].[OH:16][C:15]([CH:17]([C:19]1[CH:32]=[CH:31][CH:30]=[C:21]([C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])[CH:20]=1)[CH3:18])=[O:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623045Boc-serinol ketoprofen2×

Product 1

HCID 86623046Serinol ketoprofen Hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-serinol-ketoprofen (0.428 mmol) was dissolved in dichloromethane (1 ml), and 4 N hydrochloric acid/ethyl acetate (4 ml) was added thereto under ice-cooling, followed by stirring for 2 hours while gradually returning to room temperature. After confirming disappearance of Boc-serinol-ketoprofen by TLC, diethyl ether and hexane were added thereto, and the resulting precipitate was centrifuged. The thus obtained precipitate was dried under reduced pressure to give the titled compound (243.6 mg, qu.). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. customwhile gradually returning to room temperature
  3. additionwere added
  4. customThe thus obtained precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-eaa01563653c436caeac4284f6056bf6
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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