Sodium Hydroxide → HCID 178434012, compound

HRID 49388Notes

Reaction equation

HRID 49388 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](=O)[NH2:19])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CO[C:24](OC)([N:26](C)C)[CH3:25].O.[NH2:32]N.[OH-].[Na+]>O>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:26][C:24]([CH3:25])=[N:32][N:19]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 5222140tert-butyl N-[2-[4-(2-amino-2-oxoethyl)phenoxy]ethyl]carbamate

Product 1

HCID 178434012HCID 178434012, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

tert-Butyl-[2-(4-carbamoylmethyl-phenoxy)-ethyl]-carbamate (605 mg, 2.05 mmol) and N,N-dimethylacetamide dimethylacetal (5 ml) were combined and heated to about 120° C. for about ninety minutes. The orange solution was then allowed to cool to room temperature and was concentrated in vacuo. The resulting oil was then dissolved in acetic acid (6 ml), and hydrazine hydrate (0.20 ml, 4.10 mmol) was added to the solution. The mixture was heated to about 90° C. for about ninety minutes and was then poured into water and brought to pH 7 by adding 5M sodium hydroxide. The material was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (silica gel; chloroform to 4% methanol/chloroform) to afford 403 mg (59% yield) of the desired product. LRMS ([M+H]+)=333.2.

Workup

  1. temperatureto cool to room temperature
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe resulting oil was then dissolved in acetic acid (6 ml)
  4. temperatureThe mixture was heated to about 90° C. for about ninety minutes
  5. customThe material was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material was purified by column chromatography (silica gel; chloroform to 4% methanol/chloroform)

Sources & evidence

ORD record
ord-9d8c8ce6fe534ca78ef11d6266aeae7b
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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