Hydrochloric Acid → Cryptophycin 55

HRID 842453Notes

Reaction equation

HRID 842453 reaction equation
[CH3:1][C@H:2]([C@H:39]1[O:41][C@@H:40]1[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C@H:3]1[O:22][C:20](=[O:21])[C@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[O:18][C:16](=[O:17])[C:15]([CH3:28])([CH3:27])[CH2:14][NH:13][C:11](=[O:12])[C@@H:10]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:37][CH3:38])=[C:34]([Cl:36])[CH:35]=2)[NH:9][C:7](=[O:8])[CH:6]=[CH:5][CH2:4]1.[ClH:48].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][C@H:2]([C@@H:39]([OH:41])[C@@H:40]([Cl:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:3]1[O:22][C:20](=[O:21])[C@H:19]([CH2:23][CH:24]([CH3:25])[CH3:26])[O:18][C:16](=[O:17])[C:15]([CH3:28])([CH3:27])[CH2:14][NH:13][C:11](=[O:12])[C@@H:10]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:37][CH3:38])=[C:34]([Cl:36])[CH:35]=2)[NH:9][C:7](=[O:8])[CH:6]=[CH:5][CH2:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 9939639Cryptophycin 52

Product 1

HCID 9896488Cryptophycin 55Yield 48%

Procedure

To a solution of Cryptophycin 52 (6 mg, 0.009 mol, Example 22 or 22A) in 0.6 mL of 2:1 1,2-dimethoxymethane/water was added 2 μL of 12 N HCl. The solution was allowed to stir at room temperature for 20 h, neutralized with potassium carbonate, filtered through a 5μ filter, and evaporated. The acetonitrile-soluble material was purified by reverse-phase HPLC on C18 (250×10 mm column) using 4:1 MeOH/H2O to obtain 3.0 mg of Cryptophycin 55 (48%).

Workup

  1. filtrationfiltered through a 5μ filter
  2. customevaporated
  3. customThe acetonitrile-soluble material was purified by reverse-phase HPLC on C18 (250×10 mm column)

Sources & evidence

ORD record
ord-ad2b3cdb44db4dc69813b6d803a9c562
Source dataset
uspto-grants-2002_04
Patent number
US06376230B1

Reaction notes

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