Iodine → HCID 25009595, compound

HRID 888680Notes

Reaction equation

HRID 888680 reaction equation
II.[CH2:3]([C@@H:10]1[C@@H:24]([OH:25])[CH2:23][C:22](=[O:26])[O:21][C@H:20](/[CH:27]=[CH:28]/[CH2:29][CH2:30][S:31]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:19][C:18](=[O:51])[NH:17][C@H:16]([CH3:52])[C:15](=[O:53])[NH:14][C@H:13]([CH2:54][S:55]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:12](=[O:75])[NH:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CO>[CH2:3]([C@H:10]1[NH:11][C:12](=[O:75])[C@@H:13]2[NH:14][C:15](=[O:53])[C@@H:16]([CH3:52])[NH:17][C:18](=[O:51])[CH2:19][C@@H:20]([CH:27]=[CH:28][CH2:29][CH2:30][S:31][S:55][CH2:54]2)[O:21][C:22](=[O:26])[CH2:23][C@@H:24]1[OH:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 59223140HCID 59223140, compound

Product 1

HCID 25009595HCID 25009595, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a stirred solution of iodine (99 mg, 0.39 mmol) in CH2Cl2/MeOH (9:1, 110 mL) was added dropwise a solution of 6D (40 mg, 0.0039 mmol) in CH2Cl2/MeOH (9:1, 60 mL) over 30 min, the reaction mixture was then allowed to stir for a further 30 min after which time sodium thiosulfate (40 mL, 0.05 M) was added. The layers were separated and the product was extracted with CH2Cl2 (3×25 ml) dried over MgSO4 and the solvent was removed in vacuo. Purification was then carried out by column chromatography on silica gel (1-5% MeOH/CH2Cl2) which gave an inseparable mixture of isomers 7D & 7D′ (1:1, 11 mg, 0.02 mmol, 54%).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe product was extracted with CH2Cl2 (3×25 ml)
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification
  7. customgave

Sources & evidence

ORD record
ord-59aec32c77b94f5ca7e94edd1f34e0ec
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

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