Triethylamine → HCID 69672526, compound

HRID 1751682Notes

Reaction equation

HRID 1751682 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([O:12][CH:13]([F:15])[F:14])[CH:6]=1)=[O:4].[C:16]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(N(CC)CC)C>CC#N.CCOC(C)=O>[N:23]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([O:27][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([O:12][CH:13]([F:15])[F:14])[CH:6]=1)=[O:4])=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 86708802HCID 86708802, compound

Product 1

HCID 69672526HCID 69672526, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(4-bromo-3-(difluoromethoxy)phenyl)ethanone (6.65 mmol) and Boc-proline (1.72 g, 7.98 mmol) were suspended in MeCN (13 mL) and triethylamine (1.00 mL, 7.32 mmol) was added. The reaction mixture was stirred at RT for 14 h, then diluted with EtOAc. The organic solution was washed with water saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (19% to 40% EtOAc/Hex) to afford (S)-2-(2-(4-bromo-3-(difluoromethoxy)phenyl)-2-oxoethyl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate (2.48 g, 78% over 4 steps).

Workup

  1. washThe organic solution was washed with water saturated aqueous NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica column chromatography (19% to 40% EtOAc/Hex)

Sources & evidence

ORD record
ord-7d0024c4d69e4d81a7ef406a1f0198cc
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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