HCID 67319271, compound → HCID 11455037, compound

HRID 1261867Notes

Reaction equation

HRID 1261867 reaction equation
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[C@H:26]([O:37][C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[C@@H:25]2[O:48][C:49]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:50])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1>ClCCl>[CH2:41]([O:40][C:38]([O:37][C@@H:26]1[C@H:25]([O:48][C:49]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:50])[C@@H:24]([CH2:23][OH:22])[O:28][C@H:27]1[N:29]1[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]1=[O:31])=[O:39])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 1

HCID 67319271HCID 67319271, compound

Product 1

HCID 11455037HCID 11455037, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 4u (370 mg, 460 μmol) in dichloromethane (50 mL) was added DCA (1.5 mL). The mixture was stirred for 10 minutes, and washed with 5% aqueous NaHCO3 (3×50 mL). The aqueous layer was back-extracted with dichloromethane (10 mL), and the combined organic layer was dried over Na2SO4, filtered to separate Na2SO4, and dried under reduced pressure. The residue was purified by silica gel chromatography (eluent: 0 to 4% methanol in dichloromethane) to give the objective compound 5u (200 mg, 87%) as white foam.

Workup

  1. washwashed with 5% aqueous NaHCO3 (3×50 mL)
  2. extractionThe aqueous layer was back-extracted with dichloromethane (10 mL)
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customto separate Na2SO4
  6. customdried under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluent: 0 to 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-825fdbba53cf49d5929a946192f94838
Source dataset
uspto-grants-2013_06
Patent number
US08470987B2

Reaction notes

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