Methanol → HCID 53852971, compound

HRID 849574Notes

Reaction equation

HRID 849574 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:19])[NH:12][C@H:13]([CH3:18])[C:14]([O:16]C)=[O:15])[S:2]1.CO.[OH-].[Na+]>O1CCCC1>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:19])[NH:12][C@H:13]([CH3:18])[C:14]([OH:16])=[O:15])[S:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54182614HCID 54182614, compound

Product 1

HCID 53852971HCID 53852971, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was effected as described in Example 48, but using 1.74 g of methyl 2(R)-{3-[4-(1,2-dithiolan-3-yl)butyl]ureido}propionate (prepared as described in Example 70), 30 ml of methanol, 22 ml of tetrahydrofuran and 17.0 ml of a 1N aqueous solution of sodium hydroxide. The solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue. After neutralisation with 2N aqueous hydrochloric acid, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. The residue was recrystallized from ethyl acetate, to give 0.56 g of the title compound as yellow crystals, melting at 131 to 134° C.

Workup

  1. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  2. additionWater was added to the residue
  3. extractionAfter neutralisation with 2N aqueous hydrochloric acid, the mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEthyl acetate was removed from the
  7. extractionextract by distillation under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7579ffba89fc49978d63ab98f2793190
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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