Sodium Hydroxide → HCID 70549385, compound

HRID 2058172Notes

Reaction equation

HRID 2058172 reaction equation
[NH2:1][C:2]1([O:11][CH:10]=[CH:9][CH2:8]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].[C:14]([O:18][C:19](ON=C(C1C=CC=CC=1)C#N)=[O:20])([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1.O>[C:14]([O:18][C:19]([NH:1][C:2]1([O:11][CH:10]=[CH:9][CH2:8]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 70550517HCID 70550517, compound

Product 1

HCID 70549385HCID 70549385, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

5.0 pts. by wt. of 2-amino-furfurylacetic acid (Rohm and Haas, Netherlands Application No. 66,07754) in 100 pts. by vol. of 80 percent strength aqueous dioxane are brought to pH with 4 N sodium hydroxide solution. 8.0 pts. by wt. of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile are added and the mixture is warmed to 70° for 2 hrs. During this time, the above pH is maintained by adding 4 N sodium hydroxide solution. Thereafter, 80 pts. by vol. of water are added, the dioxane is stripped off and the reaction mixture is extracted several times with ethyl acetate. The aqueous phase is brought to pH 4 with 10 percent strength citric acid, and is saturated with sodium chloride and extracted by shaking with ethyl acetate. The ethyl acetate phases are dried over sodium sulphate and concentrated. The residue is recrystallized from a little abs. carbon tetrachloride. 4.3 pts. by wt. of 2-t-butoxycarbonylamino-furfurylacetic acid of melting point 99°-101° are obtained.

Workup

  1. temperaturethe mixture is warmed to 70° for 2 hrs
  2. temperatureDuring this time, the above pH is maintained
  3. extractionthe reaction mixture is extracted several times with ethyl acetate
  4. extractionextracted
  5. dry with materialThe ethyl acetate phases are dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from a little abs

Sources & evidence

ORD record
ord-f9dd33787ac14cebaaa427e5c2549e0b
Source dataset
uspto-grants-1980_07
Patent number
US04215118

Reaction notes

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