HCID 57514173, compound → HCID 57514175, compound

HRID 2362575Notes

Reaction equation

HRID 2362575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 57514173HCID 57514173, compound

Product 1

HCID 57514175HCID 57514175, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(3-bromophenyl)-1-hydroxypropan-2-ylcarbamate (CD1; R4=Me) (1.5 g, 4.6 mmol) in EtOAc (150 mL) at reflux was added IBX (3.82 g, 13.6 mmol, 3 eq). Reflux was continued for another 2 h and then the mixture was cooled to RT. The white precipitate was filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel by eluting with EtOAc/hexanes to give 1.0 g (66%) of tert-butyl 2-(3-bromophenyl)-1-oxopropan-2-ylcarbamate (CD2; R4=Me) as a colorless oil. 1H NMR (CDCl3) δ 9.42 (s, 1H), 7.69 (m, 1H), 7.60 (m, 1H), 7.55-7.40 (m, 2H), 5.85 (bs, 1H), 1.96 (s, 3H), 1.56 (s, 9H).

Workup

  1. additionwas added IBX (3.82 g, 13.6 mmol, 3 eq)
  2. temperatureReflux
  3. filtrationThe white precipitate was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica gel
  6. washby eluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-85977c88d8fd40b383503bcb017a7c96
Source dataset
uspto-grants-2014_04
Patent number
US08691833B2

Reaction notes

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