Bromine → HCID 76542806, compound

HRID 1360998Notes

Reaction equation

HRID 1360998 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:11][CH:10]=2)[S:3]1.[Br:27]Br>C(O)(=O)C>[Br:27][C:11]1[CH:10]=[C:9]([CH:8]=[C:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 24408BromineHCID 76542805HCID 76542805, compound

Product 1

HCID 76542806HCID 76542806, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-naphthalen-1-yloxy]pentanoic acid (example 292, 185 mg, 0.5 mmol) was treated with an equimolar amount of bromine in acetic acid (10 mL). Stirring at RT for 14 days followed by evaporation to dryness afforded a mixture of the brominated compound and unchanged starting material. Purification by preparative HPLC on a C18 column using acetonitrile and water as eluent afforded 8 mg of the title compound.

Workup

  1. customfollowed by evaporation to dryness
  2. customafforded
  3. additiona mixture of the brominated compound
  4. customPurification by preparative HPLC on a C18 column

Sources & evidence

ORD record
ord-cccabfba891f43bcb1d26a9fa0cc8235
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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