Dipropylamine → 3-(Dipropylcarbamoyl)benzoic acid

HRID 1014863

Reaction equation

HRID 1014863 reaction equation
C(OC(N1C[C@H](O)C[C@@H]1C(O)=O)=O)(C)(C)C.[CH2:17]([N:20]([CH2:33][CH2:34][CH3:35])[C:21]([C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([O:28]C)=[O:27])=[O:22])[CH2:18][CH3:19].COC(C1C=C(C=CC=1)C(O)=O)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCCC)CC>CN(C=O)C.C(OCC)(=O)C>[CH2:33]([N:20]([CH2:17][CH2:18][CH3:19])[C:21]([C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([OH:28])=[O:27])=[O:22])[CH2:34][CH3:35]

Participants

8

Reactant 5

HCID 8902DipropylamineHCID 182776Benzoic acid, 3-((dipropylamino)carbonyl)-, methyl esterHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 688616N-Boc-cis-4-hydroxy-D-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1827693-(Dipropylcarbamoyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step E (1): Methyl 3-(dipropylcarbamoyl)benzoate. To a solution of 3-(methoxycarbonyl)benzoic acid (6.7 g, 37.2 mmol) in DMF (60 mL) was added HATU (17.0 g, 44.7 mmol) and dipropylamine (9.4 g, 93 mmol) and the reaction mixture was stirred at rt overnight. Ethyl acetate (600 mL) was added and the mixture was washed with H2O, dried and concentrated to give the title compound was used in the next step without purification.

Workup

  1. washthe mixture was washed with H2O
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0756099cc8204c859264f0923d623d67
Source dataset
uspto-grants-2011_07
Patent number
US07981913B2

Linked notes

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