Hydrochloric Acid → HCID 12001784, compound

HRID 1715454Notes

Reaction equation

HRID 1715454 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[C@@H:10]([C:33](=[O:50])[N:34]([CH2:38][C:39]2[CH:44]=[C:43]([CH2:45][CH2:46][O:47][CH3:48])[CH:42]=[CH:41][C:40]=2[Cl:49])[CH:35]2[CH2:37][CH2:36]2)[CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)Cl>[Cl:49][C:40]1[CH:41]=[CH:42][C:43]([CH2:45][CH2:46][O:47][CH3:48])=[CH:44][C:39]=1[CH2:38][N:34]([CH:35]1[CH2:37][CH2:36]1)[C:33]([C@@H:10]1[C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:25]([Cl:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=3[Cl:30])=[CH:16][CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9]1)=[O:50]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 14798Sodium HydroxideHCID 68507201HCID 68507201, compound

Product 1

HCID 12001784HCID 12001784, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound D5 (279 mg, 0.375 mmol) was dissolved in CH2Cl2 (3 mL). The sol. was cooled to 0° C., and HCl (4M in dioxane, 1.00 mL) was added. The mixture was stirred at 0° C. for 1 h. HCl (4M in dioxane, 1.00 mL) was added again, and the mixture was stirred for 2 h at rt. HCl (4M in dioxane, 1.00 mL) was added again, and the mixture was stirred for 3 h at rt. Aq. 1M NaOH was added until the mixture was slightly basic. The mixture was filtered over Isolute®. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (MeOH/CH2Cl2 1:19) yielded the title compound (120 mg, 50%). LC-MS: tR=0.96 min, ES+=645.49.

Workup

  1. stirringthe mixture was stirred for 2 h at rt
  2. stirringthe mixture was stirred for 3 h at rt
  3. filtrationThe mixture was filtered over Isolute®
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (MeOH/CH2Cl2 1:19)

Sources & evidence

ORD record
ord-e19e78fe61104edb9061504d73430085
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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