Tetrahydrofuran → HCID 18947540, compound

HRID 327266Notes

Reaction equation

HRID 327266 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:8]2[CH2:35][C:36]([CH2:43][CH3:44])([CH2:41][CH3:42])[C:37]([O:39]C)=[O:38])=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([C:28](=[O:34])[CH2:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[C:8]2[CH2:35][C:36]([CH2:41][CH3:42])([CH2:43][CH3:44])[C:37]([OH:39])=[O:38])=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18947572HCID 18947572, compound

Product 1

HCID 18947540HCID 18947540, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

The compound from Step E was hydrolysed using THF (2.5 mL), MeOH (0.6 mL) and NaOH (1N, 1.5 mL). The solution was heated at 70° C. for 2 weeks. The reaction was neutralized by addition of Na4OAc buffer (20 mL of 25% w/v) and extracted with EtOAc (3×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (eluant: EtOAc-hexane-HOAc (250:750:1)) to give the title compound.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (eluant: EtOAc-hexane-HOAc (250:750:1))

Sources & evidence

ORD record
ord-37a22f6dbd8144ab8d400145459dadeb
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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