2-(1,1-Dimethylethyl) 7-methyl 6,8-dioxo-2,5-diazaspiro[3.5]nonane-2,7-dicarboxylate → HCID 59558355, compound

HRID 1175136Notes

Reaction equation

HRID 1175136 reaction equation
COC([CH:5]1[C:20](=[O:21])[CH2:19][C:8]2([CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)[NH:7][C:6]1=[O:22])=O>C(#N)C.O>[C:15]([O:14][C:12]([N:10]1[CH2:11][C:8]2([CH2:19][C:20](=[O:21])[CH2:5][C:6](=[O:22])[NH:7]2)[CH2:9]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

3

Reactant 1

HCID 595585502-(1,1-Dimethylethyl) 7-methyl 6,8-dioxo-2,5-diazaspiro[3.5]nonane-2,7-dicarboxylate

Product 1

HCID 59558355HCID 59558355, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

6,8-Dioxo-2,5-diaza-spiro[3.5]nonane-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester (1.1 g; 3.5 mmol) is refluxed in acetonitrile/water (18 ml/2 ml) for 50 minutes and evaporated to dryness. The residue is triturated with CH2Cl2 to deliver the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6): Keto-enol tautomerism. 10.70 (s, 1H); 8.75 (s, 0.5H); 7.55 (s, 0.5H); 4.85 (s, 1H); 3.94 (bd, 2H); 3.86 (bd, 2H); 3.78 (bs (2H); 1.40 (s, 9H); MS (m/z) ES+: 255 (25; MH+); 199 (100).

Workup

  1. customevaporated to dryness
  2. customThe residue is triturated with CH2Cl2

Sources & evidence

ORD record
ord-eb66dc7f04bd427cafb1bf2ebfd3af9a
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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