Water → HCID 11845474, compound

HRID 1724777Notes

Reaction equation

HRID 1724777 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[NH:15][CH:16]=2)=[CH:6][CH:5]=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:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 11299678HCID 11299678, compound

Product 1

HCID 11845474HCID 11845474, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (0.049 mL, 0.962 mmol) was added dropwise over 5 minutes to a stirring solution of 39 (0.200 g, 0.802 mmol) in acetic acid (2.5 mL). When the reaction was judged complete by HPLC (30 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. 0.1520 g.(57.7%) of 70 was obtained as a fluffy white solid. 1H (CD3OD, 400 MHz): δ 7.22 (2H, d, J=8.8 Hz), 7.12 (2H, d, J=8.8 Hz), 6.65 (1H, s), 2.81 (2H, t, J=7.3 Hz), 2.67 (2H, t, J=7.3 Hz) ppm. Partial 13C (CD3OD, 100 MHz): δ 163.33, 141.42, 132.54, 131.03, 129.18, 124.73, 117.15, 105.84, 36.72, 29.04 ppm. DEPT (CD3OD, 100 MHz): CH2 carbons: 36.72, 29.04; CH carbons: 131.03, 129.18, 117.15 ppm. HPLC: 10.484 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-f7aecd929b15421e8cf0215f9ddd0a22
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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