Water → HCID 19874469, compound

HRID 465367Notes

Reaction equation

HRID 465367 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]([C:22]#[N:23])[C:17](=[O:21])[NH:18][C:19]=2[CH3:20])=[CH:10][CH:9]=1)([OH:3])=[O:2].C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[O:33].O>CN(C=O)C>[CH2:35]([O:34][C:32]([O:2][C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]([C:22]#[N:23])[C:17](=[O:21])[NH:18][C:19]=2[CH3:20])=[CH:10][CH:9]=1)=[O:3])=[O:33])[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 19874473HCID 19874473, compound

Product 1

HCID 19874469HCID 19874469, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 820 mg (2.6 mmol) of 5-(4-carboxypropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (prepared as described in Example 2 above), 750 μl (5.38 mmol) of triethylamine, and 15 ml of DMF is cooled in an ice-water bath while stirring under N2. A solution of 540 mg (3.9 mmol) of isobutyl chloroformate in 5 ml of DMF is added dropwise. After 4 hr of stirring at 0°C., the reaction mixture is poured into water (75 ml), and extracted with EtOAc (2×50 ml). The combined EtOAc extracts are washed with water, dried (MgSO4), filtered and the solvent removed to leave 800 mg of 5-(4-isobutyloxycarbonyloxycarbonylpropoxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile as a tan-colored solid. 1H-NMR (CDCl3) δ1.00 (d, 6H); 1.60 (m, 1H); 2.16 (m, 2H); 2.50 (s, 3H); 2.70 (t, 2H); 4.10 (m, 4H); 6.93 (d, H); 7.20 (d, 2H); 7.80 (s, 2H).

Workup

  1. stirringAfter 4 hr of stirring at 0°C.
  2. extractionextracted with EtOAc (2×50 ml)
  3. washThe combined EtOAc extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-377856b011854458bc1fc8ba7cbae4c9
Source dataset
uspto-grants-1992_10
Patent number
US05153209

Reaction notes

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