Water → HCID 57435156, compound

HRID 1434813Notes

Reaction equation

HRID 1434813 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[NH:15][CH:16]=1.O>C(O)(=O)C.CCOC(C)=O>[Br:1][C:16]1[NH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=1[CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[Br:3]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 11845472HCID 11845472, compound

Product 1

HCID 57435156HCID 57435156, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (0.021 mL, 0.414 mmol) was added dropwise over 5 minutes to a stirring solution of 65 (0.1014 g, 0.345 mmol) in acetic acid (1.1 mL). When the reaction was judged complete by HPLC (20 min), H2O was added, and the solid that precipitated was filtered off and washed with H2O. The light purple solid that was obtained was dissolved in EtOAc, washed with Na2SO3 and H2O, then dried with Na2SO4, filtered, and concentrated. The product was purified by preparative reverse phase HPLC with 40:60 H2O:CH3CN (w/0.05% TFA); 20 mL/min.; λ=214 nM. 0.0574 g (44.6%) of 173 was obtained as a fluffy pale pink solid. 1H (CD3OD, 400 MHz): δ 7.50 (1H, d, J=7.8 Hz), 7.24-7.00 (3H, m), 6.68 (1H, s), 2.92 (2H, t, J=7.8 Hz), 2.67 (2H, t, J=−7.8 Hz) ppm. Partial 13C (CD3OD, 100 MHz): δ 163.25, 141.86, 133.73, 131.85, 128.89, 128.54, 125.26, 124.68, 117.16, 105.89, 37.91, 27.62 ppm. DEPT (CD3OD, 100 MHz): CH2 carbons: 37.91, 27.62; CH carbons: 133.73, 131.85, 128.89, 128.54, 117.16 ppm. HPLC: 10.473 min.

Workup

  1. additionwas added
  2. customthe solid that precipitated
  3. filtrationwas filtered off
  4. washwashed with H2O
  5. customThe light purple solid that was obtained
  6. washwashed with Na2SO3 and H2O
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by preparative reverse phase HPLC with 40:60 H2O

Sources & evidence

ORD record
ord-c1f9a6fec7324dccaefb4a742bebb3c5
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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