4-Bromophenacyl bromide → HCID 14464824, compound

HRID 1500515Notes

Reaction equation

HRID 1500515 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][C@@H:22](C)[CH2:21][C@H:20]1[C:25]([OH:27])=[O:26])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>C(Cl)Cl.CC(N(C)C)=O>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[C:25]([O:27][CH2:7][C:6]([C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9])=[O:26])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 81531DiisopropylethylamineHCID 26596883(4S)-1-(tert-Butoxycarbonyl)-4-methyl-L-proline

Product 1

HCID 14464824HCID 14464824, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
35 °C

Procedure

To a mixture of p-bromophenacyl bromide (242 mg, 0.87 mmol) in DCM (1.5 mL) and DMA (1.5 mL), under nitrogen, was added (2S,4S)-4-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (200 mg, 0.87 mmol) and N,N-diisopropylethylamine (531.8 μL, 3.05 mmol) and the resulting mixture was stirred at 35° C. for 3 h, concentrated under vacuum, dissolved in DCM (30 mL), and washed with water (2×5 ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated under vacuum to provide the title intermediate.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutiondissolved in DCM (30 mL)
  3. washwashed with water (2×5 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-98958761438c43558b0e9510aa9bf6f7
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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