Water → HCID 22484119, compound

HRID 2181356Notes

Reaction equation

HRID 2181356 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10]3[S:11][C:12]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[C:13]([C:14](OCC)=[O:15])[C:9]=3[C:8](=[O:30])[N:7]([CH3:31])[C:6]2=[O:32])[CH2:3][CH2:2]1.O>O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:10]3[S:11][C:12]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:27])[F:29])=[C:13]([CH2:14][OH:15])[C:9]=3[C:8](=[O:30])[N:7]([CH3:31])[C:6]2=[O:32])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 69878196HCID 69878196, compound

Product 1

HCID 22484119HCID 22484119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The product of step b) (6.65 g) was dissolved in tetrahydrofuran (200 mls) and LiA1H(OtBu)3 (43 mls, 1M in tetrahydrofuran) was added. The reaction mixture was heated at 60° C. for 18 hrs. Water was then added and the reaction mixture was concentrated to dryness in vacuo. The residue was extracted into ethyl acetate and the solution was dried over magnesium sulphate, filtered, and concentrated in vacuo to a greenish solid which was ultrasonicated in isohexanes for 3 hrs before being collected via filtration to yield 2.76 g of the subtitle compound as a green solid.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo
  2. extractionThe residue was extracted into ethyl acetate
  3. dry with materialthe solution was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a greenish solid which
  6. customwas ultrasonicated in isohexanes for 3 hrs
  7. filtrationbefore being collected via filtration

Sources & evidence

ORD record
ord-4fe979eba8074a89a62e4a3e382db4fc
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

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