Acetic Acid → HCID 15229452, compound

HRID 274419Notes

Reaction equation

HRID 274419 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:23]=[N:22][CH:21]=[CH:20][N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:8]2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33]C)=[O:32])=[CH:4][CH:3]=1.CO.[Li+].[OH-].C(O)(=O)C>C1COCC1.O.C([O-])(=O)C.[NH4+]>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:23]=[N:22][CH:21]=[CH:20][N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:8]2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([OH:33])=[O:32])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 15229451HCID 15229451, compound

Product 1

HCID 15229452HCID 15229452, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 517165Ammonium AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The compound from Step 2 (416 mg) was hydrolysed by dissolving it in THF (4 mL), MeOH (2 mL), and 2N LiOH (1.5 mL). The solution was heated at 70° C. for 5 hours. The mixture was cooled to room temperature, diluted with H2O (50 mL), acidified with glacial acetic acid to pH 5, and diluted with 25% aqueous ammonium acetate (50 mL). The mixture was extracted with ethyl acetate (50 mL), washed with brine (50 mL), dried (MgSO4), and evaporated to dryness to provide the title compound as a white solid; m.p. 173°-175° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (50 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0643496b351c41ce8e27080c7b386436
Source dataset
uspto-grants-1995_02
Patent number
US05389650

Reaction notes

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