Diisopropylamine → HCID 22350078, compound

HRID 896659Notes

Reaction equation

HRID 896659 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCN=C=NCCCN(C)C.[CH:26]([NH:29]C(C)C)([CH3:28])[CH3:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C.[Cl-].[NH4+].C(OCC)(=O)C>[CH:26]([NH:29][C:12](=[O:14])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)([CH3:28])[CH3:27]

Participants

8

Reactant 3

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5723454-Mesylphenylacetic acid

Product 1

HCID 22350078HCID 22350078, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (4-methanesulfonyl-phenyl)-acetic acid (2.5 g, 11.7 mmol) in CH2Cl2 (20 mL) was added EDCI (2.46 g, 12.9 mmol) followed by diisopropyl amine (1.2 mL) and DMAP (140 mg, 1.2 mmol). After 18 h at 21° C., the resulting reaction mixture was diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate/THF, 35:60:5) provided the title compound as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate/THF, 35:60:5)

Sources & evidence

ORD record
ord-f33d0b8476254244bea9a1eff71457b8
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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