Dichloromethane → HCID 71696476, compound

HRID 2272875Notes

Reaction equation

HRID 2272875 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 whole is stirred at ambient temperature for 30 minutes. The reaction mixture is subsequently diluted in dichloromethane and washed in succession with a 1N HCl solution, a saturated NaHCO3 solution and then a saturated NaCl solution until a neutral pH is reached. The organic phase is subsequently dried over magnesium sulphate, filtered and evaporated. The crude product so obtained is purified on silica gel (dichloro-methane/methanol gradient). The solid is subsequently dissolved in dichloromethane, and 2 mL of 1N ethereal hydrogen chloride are added. The whole is stirred for one hour and then evaporated to dryness. The hydrochloride so obtained is dissolved in a water/acetonitrile mixture until completely dissolved and is then lyophilised.

Workup

  1. washwashed in succession with a 1N HCl solution
  2. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product so obtained
  6. customis purified on silica gel (dichloro-methane/methanol gradient)
  7. dissolutionThe solid is subsequently dissolved in dichloromethane
  8. addition2 mL of 1N ethereal hydrogen chloride are added
  9. stirringThe whole is stirred for one hour
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-2c6ce9b87b6f45aeb0256b9573f78b33
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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