Sodium hydride → HCID 86590907, compound

HRID 1370272Notes

Reaction equation

HRID 1370272 reaction equation
[H-].[Na+].[C:3]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.Cl[CH:20]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C@H:30]2[O:34][N:33]=[C:32]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[CH2:31]2)=[O:29])=[CH:23][CH:22]=1>CN(C=O)C>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([C:32]2[CH2:31][C@@H:30]([C:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([CH:20]([N:10]([C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])[C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[CH:22][CH:23]=3)=[O:29])[O:34][N:33]=2)[CH:36]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 69194039HCID 69194039, compound

Product 1

HCID 86590907HCID 86590907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

) NaH (0.047 mol) was added portionwise to a solution of bis(1,1-dimethylethyl) imidodicarbonate (0.023 mol) in DMF (250 ml), stirred at RT (H2 gas evolution). The mixture was stirred for 30 minutes at RT. (5S)-N-[4-(chlorophenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide monohydrochloride (0.0233 mol) was added portionwise and the resulting reaction mixture was stirred vigorously for 1 hour at RT (H2 gas evolution). The solvent was evaporated under reduced pressure. The residue was partitioned between water and CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated under reduced pressure, yielding 1,1-dimethylethyl (5S)-[[4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]phenyl]phenylmethyl][(1,1-dimethylethoxy)carbonyl]carbamate (compound 501).

Workup

  1. stirringThe mixture was stirred for 30 minutes at RT
  2. customthe resulting reaction mixture
  3. stirringwas stirred vigorously for 1 hour at RT (H2 gas evolution)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was partitioned between water and CH2Cl2
  6. dry with materialThe separated organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-933ea7ea1b8948799e183b2d03cd1de9
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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