Sodium Hydroxide → HCID 59909759, compound

HRID 2183034Notes

Reaction equation

HRID 2183034 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:31])=[C:25]([C:27]([O:29]C)=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:31])=[C:25]([C:27]([OH:29])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59909776HCID 59909776, compound

Product 1

HCID 59909759HCID 59909759, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazole-4-carboxylate (Preparation 71) (1.00 g, 2.26 mmol) in 1,4-dioxane (10 ml) was treated with an aqueous sodium hydroxide solution (1N, 1.5 ml) and stirred at room temperature for 4 hours. Further aqueous sodium hydroxide (1N, 3.0 ml) was added and the mixture was stirred for 20 hours. The solvent was removed under reduced pressure and the residue was dissolved in water and washed with ethyl acetate. The layers were separated and the aqueous layer was acidified with solid citric acid then extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulphate, filtered and the solvent was removed under reduced pressure to afford the title compound as a white foam (0.83 g).

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washwashed with ethyl acetate
  5. customThe layers were separated
  6. extractionthen extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fad36a25ea094edc8ea20029ce4168cc
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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