Hydrochloric Acid → 3-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 417381

Reaction equation

HRID 417381 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:50][CH2:51][C:52]([C:54]1[CH:59]=[CH:58][C:57]([Br:60])=[CH:56][CH:55]=1)=[O:53]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19]([C:22](=[O:24])[NH:50][CH2:51][C:52]([C:54]2[CH:59]=[CH:58][C:57]([Br:60])=[CH:56][CH:55]=2)=[O:53])[CH2:18]1)=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 216392-Amino-1-(4-bromophenyl)ethanoneHCID 81531DiisopropylethylamineHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 596115123-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-diisopropylethylamine (5.3 mL, 30.6 mmol) was added dropwise to a mixture of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (2.2 g, 10.1 mmol), HATU (4.0 g, 10.5 mmol), the HCl salt of 2-amino-1-(4-bromophenyl)ethanone (2.4 g, 9.6 mmol), and DMF (40 mL), and stirred at ambient condition for 1 hour. Most of the volatile component was removed in vacuo, and the resulting residue was dissolved in ethyl acetate (150 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a white foam-like solid (3.5 g, 90%). m/z 432.9, 434.9 (M+Na)+.

Workup

  1. customMost of the volatile component was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0baad03097534a28b6b5b4bc17b31fd3
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Linked notes

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