Sodium Hydroxide → HCID 491098, compound

HRID 392975Notes

Reaction equation

HRID 392975 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]([O:32]C)=[O:31])=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]([OH:32])=[O:31])=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22660776HCID 22660776, compound

Product 1

HCID 491098HCID 491098, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 48 (0.514 g, 1.17 mmol) in tetrahydrofuran (5 mL) and ethanol (5 mL) was treated with 4 M NaOH (5 mL). The reaction mixture was refluxed for 1 h, cooled to rt, and concentrated on a rotary evaporator. The residue was dissolved in a small amount of water and made acidic with concentrated hydrochloric acid. The solid precipitate was filtered, washed with water, and dried to afford 49 as a white solid (0.52 g, 100%). ESI-MS m/e 427.3 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationconcentrated on a rotary evaporator
  3. dissolutionThe residue was dissolved in a small amount of water
  4. filtrationThe solid precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6fda0c9c5c0e47c4bbae793ca427a7e2
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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