Sodium Nitrite → HCID 178461649, compound

HRID 80973Notes

Reaction equation

HRID 80973 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]([N:21]3[CH2:26][CH2:25][C@:24]([CH2:33][C:34]([OH:37])([CH3:36])[CH3:35])([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:23][C:22]3=[O:38])[CH3:20])=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[NH2:12]>O.C(O)(=O)C>[N:12]1[C:11]2[CH:10]=[CH:9][C:8]([C:13]3[CH:14]=[CH:15][C:16]([C@@H:19]([N:21]4[CH2:26][CH2:25][C@:24]([CH2:33][C:34]([OH:37])([CH3:35])[CH3:36])([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[O:23][C:22]4=[O:38])[CH3:20])=[CH:17][CH:18]=3)=[CH:7][C:6]=2[NH:5][N:1]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 58109723HCID 58109723, compound

Product 1

HCID 178461649HCID 178461649, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of NaNO2 (0.16 g) in water (2 mL) was added dropwise to an ice-cold solution of 3-[(S)-1-(3′,4′-diamino-biphenyl-4-yl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (0.43 g) in acetic acid (10 mL). The resulting mixture was stirred with cooling for 2 h and at room temperature for another 1 h. Then, water (100 mL) was added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous NaHCO3 solution, water, and brine and dried (Na2SO4). The solvent was removed and the residue was purified by chromatography on silica gel (ethyl acetate/MeOH 98:2→80:20) to afford the title compound as a foam-like solid.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe combined organic extracts were washed with saturated aqueous NaHCO3 solution, water, and brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed
  5. customthe residue was purified by chromatography on silica gel (ethyl acetate/MeOH 98:2→80:20)

Sources & evidence

ORD record
ord-a5966ad1574a4c82b3ded1f26346a003
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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