Cesium carbonate → Alpha-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-(phenylmethoxy)1(2h)-pyridinepropanoic acid methyl ester

HRID 2355887Notes

Reaction equation

HRID 2355887 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH2:5].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:21])[CH:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][N:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:31][C:32]1=[O:36]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 10870342Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoate

Product 1

HCID 58864469Alpha-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-(phenylmethoxy)1(2h)-pyridinepropanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(di-tert-butoxycarbonylamino)-acrylic acid methyl ester (900 mg, 3.0 mmol), and 4-benzyloxy-1H-pyridin-2-one (630 mg, 1.03 equiv) in acetonitrile (2.5 mL) was added cesium carbonate (100 mg, 0.10 equiv). The resulting suspension was heated to 80° C. via microwave for 2 h. The reaction was concentrated, dissolved in water, and extracted with methylene chloride (3×). The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated to give 1.47 g (97%) which was used without purification. Mass spec.: 503.56 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in water
  3. extractionextracted with methylene chloride (3×)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give 1.47 g (97%) which
  8. customwas used without purification

Sources & evidence

ORD record
ord-79641440c345421e918459a7951cfbcc
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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