Sodium Hydroxide → HCID 14621514, compound

HRID 1651676Notes

Reaction equation

HRID 1651676 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@H:11]1[CH2:16][O:15][C@@H:14]([CH3:17])[O:13][C@H:12]1[CH2:18][O:19][C:20](=[O:28])[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@H:11]1[CH2:16][O:15][C@@H:14]([CH3:17])[O:13][C@H:12]1[CH2:18][O:19][C:20](=[O:28])[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14621512HCID 14621512, compound

Product 1

HCID 14621514HCID 14621514, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-phenylcarbamoyloxymethyl-1,3-dioxane (140 mg) in methanol (2 ml) was added 1 ml of 1N aqueous sodium hydroxide and stirred at room temperature for 90 minutes. The reaction mixture was evaporated in vacuo and the residue was neutralized by acetic acid and extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated to dryness and the crude product was purified with preparative TLC (ether : dichloromethane=1:1) to give (2R,4R,5S) -5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-4-phenylcarbamoyloxymethyl-1,3-dioxane (115 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated to dryness
  5. customthe crude product was purified with preparative TLC (ether : dichloromethane=1:1)

Sources & evidence

ORD record
ord-f233624d12df427cb1bfe95f0d87790e
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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