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

HRID 537449Notes

Reaction equation

HRID 537449 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-eca4587c6ef7402aabe287195a6bdf98
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

Loading…