Ammonia → Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

HRID 2047296Notes

Reaction equation

HRID 2047296 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(O)(C)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](=[O:15])[NH2:27])=[CH:12][C:11]=1[CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

Product 1

HCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoateYield 94.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a suspension of 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid (8.00 g, 28.7 mmol) in isopropanol (100 mL), HOBt (4.27 g, 31.6 mmol) followed by EDC hydrochloride (6.34 g, 33.1 mmol) is added. After stirring at rt for 1 h, 25% aq. ammonia (16.1 mL) is added. Stirring is continued for 30 min before the isopropanol is evaporated under reduced pressure. The remaining solution is diluted with isopropyl acetate (200 mL), washed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL) followed by water (50 mL), dried over MgSO4, filtered, concentrated and dried to give 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.5 g) as an off-white solid.

Workup

  1. additionis added
  2. stirringStirring
  3. customis evaporated under reduced pressure
  4. additionThe remaining solution is diluted with isopropyl acetate (200 mL)
  5. washwashed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-cf4c66fe557b4196b1ce716f1d5fcfb4
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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