Sodium Hydroxide → HCID 131728990, compound

HRID 2428206Notes

Reaction equation

HRID 2428206 reaction equation
[OH-].[Na+].C[O:4][C:5]([C@@H:7]1[C@@H:13]([C:14]2[CH:15]=[N:16][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:18][CH:19]=2)[CH2:12][C@H:11]2[N:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@@H:8]1[CH2:9][CH2:10]2)=[O:6]>CCO>[C:37]([O:36][C:34]([N:33]1[C@H:11]2[CH2:10][CH2:9][C@@H:8]1[C@H:7]([C:5]([OH:6])=[O:4])[C@@H:13]([C:14]1[CH:15]=[N:16][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:18][CH:19]=1)[CH2:12]2)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728991HCID 131728991, compound

Product 1

HCID 131728990HCID 131728990, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Aq. 1M NaOH (6.50 mL) was added to a sol. of compound D8 (1.19 g, 2.10 mmol) in EtOH (12 mL). The mixture was heated to 70° C. for 2 h. The mixture was allowed to cool to rt, and the solvents were partially removed under reduced pressure. The resulting mixture was partitioned between EtOAc and aq. 2M HCl. The phases were separated, and the aq. phase was extracted with EtOAc (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (1.07 g, 92%) that was used further without purification. LC-MS: tR=1.08 min, ES+: 551.33.

Workup

  1. temperatureto cool to rt
  2. customthe solvents were partially removed under reduced pressure
  3. customThe resulting mixture was partitioned between EtOAc and aq. 2M HCl
  4. customThe phases were separated
  5. extractionthe aq. phase was extracted with EtOAc (2×)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-a30a94245c254a59bfb5a2db7ef087a4
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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