Hydrochloric Acid → HCID 66746908, compound

HRID 1467284Notes

Reaction equation

HRID 1467284 reaction equation
[C:1]([C:3]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])OC(C)(C)C)#[N:2].Cl.N1C=CC=CC=1.[C:34]([O:37][C:38](C)([CH3:42])[C:39](Cl)=O)(=[O:36])[CH3:35]>O1CCOCC1>[C:34]([O:37][C:38]([CH3:42])([CH3:39])[C:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:20]=[CH:21][CH:22]=[C:23]([N+:24]([O-:26])=[O:25])[C:3]=1[C:1]#[N:2])=[O:19])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 66747127HCID 66747127, compound

Product 1

HCID 66746908HCID 66746908, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 6-(2-cyano-3-nitrophenoxy)hexylcarbamate (333 mmol, 121 mg) (Example 225c) in dioxane (2 mL) was added con. HCl (1 mL). After 15 minutes, the solution was concentrated in vacuo and dried on high vacuum. The crude HCl salt was suspended in DCM (dry, 10 mL) and treated with pyridine (2.664 mmol, 62 μL) and 1-chloro-2-methyl-1-oxopropan-2-yl acetate (1.332 mmol, 193 μL). The reaction mixture was refluxed under a nitrogen atmosphere until clear (6 h), then cooled to room temperature and the volatiles removed in vacuo. The residue was purified on silica gel (40% to 100% EtOAc in hexanes) to give the product (117 mg, 90%) as a light yellow heavy oil. MS 392 (MH+).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customdried on high vacuum
  3. temperatureThe reaction mixture was refluxed under a nitrogen atmosphere until clear (6 h)
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified on silica gel (40% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6287bcbf314a403ea510ace11b0699ad
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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