Hydrochloric Acid → HCID 66746908, compound

HRID 711920Notes

Reaction equation

HRID 711920 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]>>[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

5

Reactant 4

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

Product 1

HCID 66746908HCID 66746908, compoundYield 90%

Procedure

To a solution of tert-butyl 6-(2-cyano-3-nitrophenoxy)hexylcarbamate (333 mmol, 121 mg) (Example 277c) in dixoane (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, 215 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-a07b34b2345545d7976d9a997bc3525b
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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