Diketene → HCID 59205058, compound

HRID 1917477Notes

Reaction equation

HRID 1917477 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C@@H:6]([NH2:15])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[Br:14])[CH3:2].[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C@H:6]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[Br:14])[NH:15][C:20](=[O:21])[CH2:19][C:18](=[O:22])[CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 7022757HCID 7022757, compound

Product 1

HCID 59205058HCID 59205058, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mL round-bottom flask charged with 31D (13.3 g, 41 mmol) in 200 mL of DCM and TEA (22.8 mL, 3 equiv.) was added diketene (31E, 8.81 mL, 50% in DCM). The reaction was stirred at ambient temperature until completion (2 h, determined by LCMS). The reaction mixture was washed with 1 N NaHSO4, brine, dried over Na2SO4 and concentrated in vacuo to afford Compound 31F as a yellow solid (15.3 g, 99%). ESI-MS: m/z 374.0 (MH+).

Workup

  1. washThe reaction mixture was washed with 1 N NaHSO4, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db7ee06834344d3e8355355a9918862f
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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