Triethylamine → Methyl 3-(4-(3-methylbutanoyl)benzamido)propanoate

HRID 1520823Notes

Reaction equation

HRID 1520823 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)=[O:5].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[NH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45].C(N(CC)CC)C>CN(C)C=O>[CH3:15][CH:2]([CH3:1])[CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:12])=[CH:13][CH:14]=1)=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 681567904-(3-Methylbutanoyl)benzoic acid

Product 1

HCID 68157349Methyl 3-(4-(3-methylbutanoyl)benzamido)propanoateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-methylbutanoyl)benzoic acid (9.5 g, 46 mmol) in N,N-dimethylformamide (80 mL) was added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (26.3 g, 69.1 mmol) at 0° C. The mixture was stirred for 40 minutes. Methyl 3-aminopropanoate hydrochloride (7.72 g, 55.3 mmol) and triethylamine (23.3 g, 230 mmol) were added and the reaction was allowed to warm to room temperature and stir for 16 hours. The reaction mixture was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography gave methyl 3-(4-(3-methylbutanoyl)benzamido)propanoate (10 g, 77%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3, δ): 7.98 (d, J=8.0 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 6.91 (s, 1H), 3.72-3.76 (m, 5H), 2.84 (d, J=6.0 Hz, 2H), 2.66-2.69 (t, J=6.0 Hz, 2H), 2.23-2.33 (m, 1H), 0.99 (d, J=6.4 Hz, 6H).

Workup

  1. stirringstir for 16 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-09f308ca4f744751a18faddd32faa4d6
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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