Ammonia → HCID 11777679, compound

HRID 2255466Notes

Reaction equation

HRID 2255466 reaction equation
[NH3:1].[CH3:2][C:3]([O:6][C:7](=[O:22])[CH2:8][N:9]([C:13]1[C:16](=[O:17])[C:15](=[O:18])[C:14]=1OCC)[CH2:10][CH:11]=[CH2:12])([CH3:5])[CH3:4]>>[CH3:2][C:3]([O:6][C:7](=[O:22])[CH2:8][N:9]([C:13]1[C:16](=[O:17])[C:15](=[O:18])[C:14]=1[NH2:1])[CH2:10][CH:11]=[CH2:12])([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 10424583HCID 10424583, compound

Product 1

HCID 11777679HCID 11777679, compoundYield 71%

Procedure

Ethanolic ammonia (25 mL) was added to a flask containing N-(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)-N-(2-propenyl)glycine 1,1-dimethylethyl ester (2.5 g, 8.5 mmol) at room temperature. After 5 hours the reaction mixture was concentrated and purified by flash chromatography (5 cm diameter, elution with 5% methanol in dichloromethane) to yield N-(2-amino-3,4-dioxo-1-cyclobuten-1-yl)-N-(2-propenyl)glycine 1,1-dimethylethyl ester as a white solid (1.6 g, 71%, mp 175°-176° C.); IR (KBr, cm-1): 3300, 3140, 1810, 1740, 1670, 1650; MS (EI): 266 (M+, 34), 210 (24), 165 (100), 109 (54), 95 (89), 68 (68); 1H NMR (DMSO, 400 MHz): δ 7.70 (br s, NH2), 5.84-5.77 (m, 1H), 5.26 (d, J=17 Hz, 1H), 5.19 (d, J=10 Hz, 1H), 4.3-4.0 (br m, 4H), 1.39 (s, 9H).

Workup

  1. concentrationAfter 5 hours the reaction mixture was concentrated
  2. custompurified by flash chromatography (5 cm diameter, elution with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-da41879d0b5a4b17ae908d3e6c397e08
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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