Sodium Hydroxide → HCID 178453715, compound

HRID 1404411Notes

Reaction equation

HRID 1404411 reaction equation
[CH3:1][C:2]([CH3:30])([O:4][C:5](=[O:29])[NH:6][CH:7]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:19][CH2:18]1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:3].[OH-].[Na+]>C1COCC1.CO>[CH3:3][C:2]([CH3:30])([O:4][C:5](=[O:29])[NH:6][CH:7]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH2:18]1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH3:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178471772HCID 178471772, compound

Product 1

HCID 178453715HCID 178453715, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(trans-4-(2,2,11,11-tetramethyl-4,9-dioxo-3,10-dioxa-5,8-diazadodecan-6-yl)cyclohexyl)acetate (0.58 g, 1.35 mmol) in THF (5 mL) and MeOH (5 mL) was added 3N NaOH (2.25 mL, 6.75 mmol). The resulting mixture was stirred at RT for 3 h. After removal of volatiles by evaporation, the residue was acidified by 0.5N HCl solution to pH ˜4.5 and extracted with EtOAc, dried over Na2SO4. Filtration and evaporation to dryness gave the acid in a quantitative yield. LC/MS: 423.1 (MNa)+.

Workup

  1. customAfter removal of volatiles
  2. customby evaporation
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation to dryness
  6. customgave the acid in a quantitative yield

Sources & evidence

ORD record
ord-86e18466f4cb429382b9f9798ddf8462
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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