Iodine → HCID 25009592, compound

HRID 888676Notes

Reaction equation

HRID 888676 reaction equation
II.[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C@@H:20]2[C:34](=[O:35])[NH:33][C@H:32]([CH2:36][S:37]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:31](=[O:57])[NH:30][C@H:29]([CH:58]([CH3:60])[CH3:59])[C@@H:28]([OH:61])[CH2:27][C:26](=[O:62])[O:25][C@H:24](/[CH:63]=[CH:64]/[CH2:65][CH2:66][S:67]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:23][C:22](=[O:87])[NH:21]2)=[CH:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CO>[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C@@H:20]2[C:34](=[O:35])[NH:33][C@@H:32]3[CH2:36][S:37][S:67][CH2:66][CH2:65][CH:64]=[CH:63][C@@H:24]([O:25][C:26](=[O:62])[CH2:27][C@H:28]([OH:61])[C@@H:29]([CH:58]([CH3:60])[CH3:59])[NH:30][C:31]3=[O:57])[CH2:23][C:22](=[O:87])[NH:21]2)=[CH:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 59223103HCID 59223103, compound

Product 1

HCID 25009592HCID 25009592, compoundYield 463.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a solution of iodine (107.2 mg, 0.42 mmol) in CH2Cl2/MeOH (9:1, 143 mL) was added dropwise a solution of 6B (48.4 mg, 0.0041 mmol) in CH2Cl2/MeOH (9:1) (70 mL) over 30 min, the reaction mixture was then allowed to stir for a further 30 min after which time sodium thiosulfate (26 mL, 0.05 M) was added. The organic phase was separated and the aqueous phase extracted with CH2Cl2 (3×20 mL). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography on silica gel (eluent 0:100-1:99-3:97 MeOH/CH2Cl2) which gave 7B (13 mg, 0.019 mmol, 46%) as a white solid: Rf 0.18 CH2Cl2/MeOH (97:3); [α]28D=−1.9 (c 0.36, CHCl3); IR (thin film) 3379 (br), 3343 (br), 2974 (m), 2931 (m), 1732 (s), 1662 (s), 1538 (m), 1519 (m), 1453 (m), 1371 (s), 1333 (m), 1310 (m), 1271 (m), 1255 (s).

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography on silica gel (eluent 0:100-1:99-3:97 MeOH/CH2Cl2) which

Sources & evidence

ORD record
ord-cfe67bdd44c84924967124026682a120
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

Loading…