Iodine chloride → HCID 131736627, compound

HRID 1481298Notes

Reaction equation

HRID 1481298 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[C:10]([CH:30]=3)[C@@H:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:12][CH2:13][CH2:14][C@@H:15]([CH3:21])[C:16](=[O:20])[NH:17][C:18]=2[CH:19]=1.[I:31]Cl>CO.C(Cl)Cl>[NH2:1][C:2]1[C:3]([I:31])=[CH:4][C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[C:10]([CH:30]=3)[C@@H:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:12][CH2:13][CH2:14][C@@H:15]([CH3:21])[C:16](=[O:20])[NH:17][C:18]=2[CH:19]=1

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 118287542HCID 118287542, compound

Product 1

HCID 131736627HCID 131736627, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To cooled (0° C.) solution of 86A (0.87 g, 2.119 mmol) in MeOH (21.19 ml) was added a solution of iodine monochloride (0.516 g, 3.18 mmol) in DCM (5.0 mL). The reaction was stirred at rt for 1 h and then it was concentrated. The residue was redissolved in EtOAc, washed with sat. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. Purification by normal phase chromatography afforded 86B (0.9 g, 79% yield) as a brown solid. MS (ESI) m/z: 537.1 (M+H)+.

Workup

  1. concentrationit was concentrated
  2. dissolutionThe residue was redissolved in EtOAc
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-d0b8fd23608c4c4db6dbdb4d63765093
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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