Water → HCID 178488167, compound

HRID 2121872Notes

Reaction equation

HRID 2121872 reaction equation
[Cl-].[OH:2][C@H:3]([CH3:15])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[NH3+:14].[N:16](OCCC(C)C)=O.O>ClCCl.C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:13][O:12][C:10]1[CH:11]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:14][N:16]=[C:5]2[CH2:4][C@H:3]([OH:2])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 8053Isoamyl NitriteHCID 69702667HCID 69702667, compound

Product 1

HCID 178488167HCID 178488167, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of the product from step C (2.66 g, 11.5 mmol) in dichloromethane (150 mL) at ambient temperature was added isoamyl nitrite (2.47 mL, 18.4 mmol, 1.6 equiv.). After 30 minutes tetrabutylammonium acetate (5.54 g, 18.4 mmol, 1.6 eq) was added and the mixture was stirred for 2 hours. Water was added to the mixture and the organic layer was separated and washed with 2 N NaOH and water. After drying and evaporation the crude product was purified by column chromatography (gradient of 20% to 40% ethyl acetate in hexane) to give an oil (1.58 g) that crystallized from ethyl acetate/hexane (1:1) to afford a solid (1.30 g, 55%): mp 89-91° C.; LC/MS (+APCI) m/z 207 (M+H).

Workup

  1. customthe organic layer was separated
  2. washwashed with 2 N NaOH and water
  3. customAfter drying
  4. customevaporation the crude product
  5. customwas purified by column chromatography (gradient of 20% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-058387576e014b6fa9806a237ace3814
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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