Ammonia → HCID 10516277, compound

HRID 1743250Notes

Reaction equation

HRID 1743250 reaction equation
N.[Na].[CH2:3]([C@:6]1([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:12])[O:10][C@H](C2C=CC=CC=2)[C@H](C2C=CC=CC=2)[N:7]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:4]=[CH2:5].[Cl-].[NH4+]>C1COCC1.C(O)C>[C:28]([O:27][C:25]([NH:7][C@:6]([CH2:32][CH:33]([CH3:35])[CH3:34])([CH2:3][CH:4]=[CH2:5])[C:11]([OH:12])=[O:10])=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 69795369HCID 69795369, compound

Product 1

HCID 10516277HCID 10516277, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

60 ml of ammonia were condensed at −78° C. Then 624 mg of sodium were added in 2 portions at an interval of 10 min. The mixture was stirred for 20 min. At −60° C., a solution of tert-butyl (3R,5S,6R)-3-allyl-3-isobutyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate 1.22 g and 1.6 ml of ethanol in 20 ml of THF was added dropwise thereto. The mixture was stirred at −45° C. for 1.5 h, and the reaction was stopped by adding solid ammonium chloride until the blue color disappeared. The ammonia is then allowed to evaporate off, and 50 ml of water are added to the residue. The THF is removed in vacuo. The aqueous is adjusted to pH 2 with 1 N HCl and extracted 3 times with 60 ml of ethyl acetate each time. The combined organic phases are dried with MgSO4. The solvents are removed in vacuo and the residue is purified by chromatography on silica gel.

Workup

  1. customcondensed at −78° C
  2. stirringThe mixture was stirred at −45° C. for 1.5 h
  3. customto evaporate off
  4. addition50 ml of water are added to the residue
  5. customThe THF is removed in vacuo
  6. extractionextracted 3 times with 60 ml of ethyl acetate each time
  7. dry with materialThe combined organic phases are dried with MgSO4
  8. customThe solvents are removed in vacuo
  9. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2593588e5f2b4c15a6c7658b6cc122f1
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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