Triethylamine → HCID 20244812, compound

HRID 647882Notes

Reaction equation

HRID 647882 reaction equation
[NH2:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[C:26]([O:30][C:31](ON=C(C1C=CC=CC=1)C#N)=[O:32])([CH3:29])([CH3:28])[CH3:27]>O1CCOCC1.O>[C:26]([O:30][C:31]([NH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 20244815HCID 20244815, compound

Product 1

HCID 20244812HCID 20244812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-amino-4-(o-nitrophenyl)butyrate (17.4 g) in 50% aqueous dioxane (130 ml) is added triethylamine (10.5 g) and 2-(tert-butyloxycarbonyloxyimino-2-phenylacetonitrile (18.7 g). The reaction mixture is stirred at room temperature for 4 hours and then diluted with water (300 ml). The mixture is extracted with ether (2×150 ml) and the aqueous phase acidified with ice-cold 2N hydrochloric acid and extracted with ethyl acetate (2×250 ml). The ethyl acetate layers are combined, washed with water (150 ml) and dried over sodium sulfate. The solvent is removed under reduced pressure to give ethyl 2-t-butyloxycarbonylamino-4-(o-nitrophenyl)butyrate, used without further purification.

Workup

  1. extractionThe mixture is extracted with ether (2×150 ml)
  2. extractionextracted with ethyl acetate (2×250 ml)
  3. washwashed with water (150 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5321860af6974b31b6987b13d3dedcc3
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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