Ethyl orthoformate → HCID 11779701, compound

HRID 1791986Notes

Reaction equation

HRID 1791986 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([C:25]1([CH:28]([NH:31][C@H:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:33])[C:29]#[N:30])[CH2:27][CH2:26]1)=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[C:25]1([C@H:28]([NH:31][C@H:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH3:33])[C:29]#[N:30])[CH2:27][CH2:26]1)[CH3:10]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86590957HCID 86590957, compound

Product 1

HCID 11779701HCID 11779701, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethyl orthoformate (0.2 mL, 1.20 mmol) and p-toluenesulfonate monohydrate (1 mg, 0.0053 mmol) were added to an ethanol (2.5 mL) solution of 2-(1-formylcyclopropyl)-2-{[(1S)-1-phenylethyl]amino}acetonitrile (102 mg, 0.447 mmol). The resulting mixture was stirred at room temperature for 2 hours and 30 minutes and then, at 50° C. for 4 hours. After cooling to room temperature, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The organic layer was washed with water and then, dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography, whereby the title compound was obtained as white crystals (40 mg, 30%, diastereomer ratio=81/19).

Workup

  1. waitat 50° C. for 4 hours
  2. temperatureAfter cooling to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography, whereby the title compound
  8. customwas obtained as white crystals (40 mg, 30%, diastereomer ratio=81/19)

Sources & evidence

ORD record
ord-6b67d968e1534cda954c23cbcb1adade
Source dataset
uspto-grants-2006_07
Patent number
US07074837B2

Reaction notes

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