Hydrochloric Acid → HCID 54691691, compound

HRID 1034220Notes

Reaction equation

HRID 1034220 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])C=C.C(OCC)(=O)[C:20](OCC)=[O:21].[O-:29][CH2:30][CH3:31].[Na+].Cl.[CH3:34]CO>O>[OH:29][C:30]1[C:20](=[O:21])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:34][C:31]=1[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 7268Diethyl OxalateHCID 7504BenzylamineHCID 15458tert-Butyl acrylateHCID 2723922Sodium ethoxideHCID 5360545Sodium2×

Product 1

HCID 54691691HCID 54691691, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of benzyl amine (7.3 ml, 0.067 mol) in dry EtOH (freshly distilled from sodium) was added tert-butyl acrylate (6.8 ml, 0.046 mol) via syringe and the resulting solution was stirred under an atmosphere of argon for 64 h at room temperature. To the solution was then added diethyl oxalate (9.90 g, 0.068 mol). The solution was then cooled to 0° C. and a freshly prepared solution of sodium ethoxide [freshly prepared from sodium (1.7 g, 0.074 mol) and 75 ml of EtOH]was added via cannula while maintaining the temperature between 0° C. and 5° C. After the addition was complete the solution was warmed to room temperature and stirred overnight. To the resulting slurry was added 100 ml of water followed by the slow addition of 30% aqueous HCl to acidify to pH=1. The suspension was then extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a light pink powder (8.37 g, 62.9%). Purification of an analytical sample by chromatography on silica gel eluting with 5/94.5/0.5 MeOH/CH2Cl2 /HOAc gave 8.67g, (65%) of the title compound as a powder. Anal calcd for C16H19NO4 : C, 66.43; H, 6.52; N, 4.84. Found: C, 66.38; H, 6.70; N, 5.10. DSC=172.2°-176.2° at 190.9 J/g.

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. additionwas added via cannula
  3. temperaturewhile maintaining the temperature between 0° C. and 5° C
  4. additionAfter the addition
  5. temperaturewas warmed to room temperature
  6. stirringstirred overnight
  7. extractionThe suspension was then extracted with CH2Cl2
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f5b9434d05042d9b1169294e72fea95
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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