Diethyl Ether → HCID 59853908, compound

HRID 2061260Notes

Reaction equation

HRID 2061260 reaction equation
[OH-].[Na+].[CH2:3]([O:5]CC)[CH3:4].Cl.[NH2:9][C@@H:10]([CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=[C:23]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH:27]=[CH:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]2=3)[CH2:19][CH2:18]1)=[O:16])[CH2:11][OH:12].C(Cl)(=O)C>O.C(OCC)(=O)C>[CH:33]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]=3[C:23](=[C:20]3[CH2:19][CH2:18][N:17]([C:15](=[O:16])[CH2:14][CH2:13][C@H:10]([NH:9][C:3](=[O:5])[CH3:4])[CH2:11][OH:12])[CH2:22][CH2:21]3)[C:29]=2[CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 68421295HCID 68421295, compound

Product 1

HCID 59853908HCID 59853908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 ml of 1 N aqueous sodium hydroxide solution, 3 ml of diethyl ether and 2 ml of ethyl acetate were added to 151 mg (0.36 mmol) of (S)-2-amino-5-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-5-oxo-1-pentanol hydrochloride. 0.04 ml (0.56 mmol) of acetyl chloride was added dropwise to the obtained solution under vigorous stirring, and they were stirred at room temperature for 2 hours. Water was added to the reaction mixture. After extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (chloroform:methanol-200:1 to 50:1) to obtain the title compound.

Workup

  1. extractionAfter extracting with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (chloroform:methanol-200:1 to 50:1)

Sources & evidence

ORD record
ord-c386780d49214a4a9fa7d5f286064551
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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