Tetrahydrofuran → HCID 9885239, compound

HRID 1975721Notes

Reaction equation

HRID 1975721 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:20]#[N:21])=[CH:15][CH:14]=1.C1C[O:30]CC1.C(=O)(O)[O-].[Na+]>Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:20]([NH2:21])=[O:30])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 19025756HCID 19025756, compound

Product 1

HCID 9885239HCID 9885239, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

2 g (5.8 mmol) of the compound from Example II are suspended in 6 ml of concentrated hydrochloric acid, and the suspension is stirred at 40° C. overnight. After cooling to room temperature, THF is added until solution is complete, and the solution is neutralised with sodium bicarbonate solution. The organic phase is separated off, dried with sodium sulphate and concentrated to a small volume in vacuo. Separation is carried out by column chromatography (silica gel 60, mobile phase: dichloromethane/ethyl acetate/glacial acetic acid 80/15/15).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase is separated off
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated to a small volume in vacuo
  5. customSeparation

Sources & evidence

ORD record
ord-923dfc23418f4a5b85a345a231aefb91
Source dataset
uspto-grants-1994_02
Patent number
US05288733

Reaction notes

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