Sodium hydride → HCID 131733310, compound

HRID 518923Notes

Reaction equation

HRID 518923 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][CH2:4]1.CC1C=CC(S(O[CH2:30][C@@H:31]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][N:32]2[S:41]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)(=[O:43])=[O:42])(=O)=O)=CC=1.[Cl-].[NH4+]>CC(OC)(C)C>[CH3:50][C:47]1[CH:48]=[CH:49][C:44]([S:41]([N:32]2[C@H:31]([CH2:30][CH:10]([C:9]([N:6]3[CH2:5][CH2:4][O:3][CH2:8][CH2:7]3)=[O:18])[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)(=[O:42])=[O:43])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 117830854HCID 117830854, compoundHCID 117831294HCID 117831294, compound

Product 1

HCID 131733310HCID 131733310, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a suspension of 1 g of NaH (60%) (25.08 mmol) in 30 mL of MTBE there are added, dropwise, a solution of 5 g of tert-butyl 3-morpholino-3-oxopropanoate (21.81 mmol) in 20 mL of anhydrous MTBE. This suspension is stirred at ambient temperature for 1 hour and then the compound obtained in Step A is added in the form of a powder. The batch is stirred at 60° C. for 30 hours. 100 mL of saturated aqueous ammonium chloride solution are added. The resulting solution is extracted with dichloromethane. The organic phase is then dried over MgSO4, filtered and concentrated to dryness. After purification by chromatography over silica gel (dichloromethane/MeOH gradient), the expected product is obtained in the form of an oil.

Workup

  1. additionthere are added
  2. stirringThe batch is stirred at 60° C. for 30 hours
  3. extractionThe resulting solution is extracted with dichloromethane
  4. dry with materialThe organic phase is then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customAfter purification by chromatography over silica gel (dichloromethane/MeOH gradient)

Sources & evidence

ORD record
ord-a7ac8f5fae1c473dab054c960a386142
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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