Triethylamine → β-Alanine, N-(1,1-dimethylethyl)-N-(4-formylbenzoyl)-, 1,1-dimethylethyl ester

HRID 537437Notes

Reaction equation

HRID 537437 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.C(Cl)(=O)C(Cl)=O.[C:18]([NH:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>ClCCl.CN(C)C=O>[C:18]([N:22]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:1](=[O:3])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 120884-Formylbenzoic acidHCID 65578Oxalyl chlorideHCID 13976268HCID 13976268, compound

Product 1

HCID 86669084β-Alanine, N-(1,1-dimethylethyl)-N-(4-formylbenzoyl)-, 1,1-dimethylethyl esterYield 103.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

N,N-dimethylformamide (25 μL) was added to a room temperature suspension of 4-carboxybenzaldehyde (2.0 g, 13 mmol) and oxalyl chloride (1.14 mL, 13.3 mmol) in dichloromethane (50 mL). The reaction was stirred at room temperature 30 minutes, then heated to reflux for 5 hours. The reaction mixture was concentrated. A solution of tert-butyl 3-(tert-butylamino)propanoate (2.68 g, 13.3 mmol) and triethylamine (1.9 mL, 13 mmol) in dichloromethane (50 mL) was added to the crude acid chloride. The mixture was stirred at room temperature overnight. The reaction was washed with water, then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to give tert-butyl 3-(N-tert-butyl-4-formylbenzamido)propanoate (4.47 g, 100%). 1H NMR (400 MHz, CDCl3, δ): 10.01 (s, 1H), 7.86-7.91 (m, 2H), 7.45-7.49 (m, 2H), 3.46-3.54 (m, 2H), 2.34-2.41 (m, 2H), 1.52 (s, 9H), 1.31 (s, 9H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated
  4. stirringThe mixture was stirred at room temperature overnight
  5. washThe reaction was washed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6a55f640e34c4c0d9b48291cbf534b13
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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