Dichloromethane → HCID 71696476, compound

HRID 518930Notes

Reaction equation

HRID 518930 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:16]([C:18]2[CH:19]=[C:20]([C:27]3[C:35]([C:36]([N:38]4[C@H:47]([CH2:48][N:49]5[CH2:54][CH2:53][O:52][CH2:51][CH2:50]5)[CH2:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[CH2:39]4)=[O:37])=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)[N:21]3[C:26]=2[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:17])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH-].[K+].[Cl:63]CCl>CO>[ClH:63].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:16]([C:18]2[CH:19]=[C:20]([C:27]3[C:35]([C:36]([N:38]4[C@H:47]([CH2:48][N:49]5[CH2:54][CH2:53][O:52][CH2:51][CH2:50]5)[CH2:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[CH2:39]4)=[O:37])=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)[N:21]3[C:26]=2[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:17])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 131733361HCID 131733361, compound

Product 1

HCID 71696476HCID 71696476, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.9 g of the compound obtained in Step C (2.3 mmol) in 4 mL of methanol there is added 0.646 g (11.5 mmol) of potassium hydroxide dissolved in 8 mL of methanol. The batch is stirred at ambient temperature for 30 minutes. The reaction mixture is then diluted with dichloromethane and washed successively with 1M HCl solution, saturated aqueous NaHCO3 solution and then brine until a neutral pH is reached. The organic phase is then dried over magnesium sulphate, filtered and evaporated. The crude product thereby obtained is purified by chromatography over silica gel (dichloromethane/methanol gradient). The solid is then dissolved in dichloromethane, and 2 mL of 1M ethereal HCl are added. The batch is stirred for 1 hour and then evaporated to dryness. The hydrochloride thereby obtained is dissolved in a mixture of water/acetonitrile until dissolution is complete, and is then lyophilised.

Workup

  1. washwashed successively with 1M HCl solution, saturated aqueous NaHCO3 solution
  2. dry with materialThe organic phase is then dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product thereby obtained
  6. customis purified by chromatography over silica gel (dichloromethane/methanol gradient)
  7. dissolutionThe solid is then dissolved in dichloromethane
  8. addition2 mL of 1M ethereal HCl are added
  9. stirringThe batch is stirred for 1 hour
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-c69ee5d748bb42e48891463f41269572
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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