Ammonia → 3-(4-Carbamoyl-2-ethyl-6-methylphenyl)propionic acid tert-butyl ester

HRID 2040804Notes

Reaction equation

HRID 2040804 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[CH2:20][CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:28]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(O)(C)C.C(Cl)Cl>[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])[NH2:28])=[CH:12][C:11]=1[CH2:20][CH3:21])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685516044-(2-Tert-butoxycarbonylethyl)-3-ethyl-5-methylbenzoic acid

Product 1

HCID 685531653-(4-Carbamoyl-2-ethyl-6-methylphenyl)propionic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-tert-butoxycarbonyl-ethyl)-3-ethyl-5-methyl-benzoic acid (36.0 g, 123 mmol) in isopropanol (400 mL), HOBT (18.3 g, 135 mmol) followed by EDC HCl (27.1 g, 142 mmol) is added. The mixture is stirred at rt for 1 h before aq. ammonia (69 mL of 25% solution) is added. Stirring is continued for 1 h before the mixture is diluted with DCM (500 mL) and washed with half sat. aq. NaHCO3 solution (3×400 mL), followed by water (400 mL). The org. extract is dried over MgSO4, filtered and concentrated. The crude product is trituated with TBME 8250 mL). The solid material is collected, washed with additional TBME (50 mL) and dried under high vacuum to give 3-(4-carbamoyl-2-ethyl-6-methyl-phenyl)-propionic acid tert-butyl ester (31.91 g) as a white solid.

Workup

  1. additionis added
  2. additionis added
  3. washwashed with half sat. aq. NaHCO3 solution (3×400 mL)
  4. extractionextract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe solid material is collected
  9. washwashed with additional TBME (50 mL)
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-bb64bb7f34fe462399024821bbe7ad4c
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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