Hydrochloric Acid → HCID 67433810, compound

HRID 577965Notes

Reaction equation

HRID 577965 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:25]=[C:24](C(=O)C)[C:23]([O:29][N:30]=[C:31]([CH3:33])C)=[C:22]([Cl:34])[C:21]=1[N:35]1[CH2:40][C@H:39]([CH3:41])[O:38][C@H:37]([CH3:42])[CH2:36]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>CCO.CCOC(C)=O>[Cl:34][C:22]1[C:21]([N:35]2[CH2:36][C@H:37]([CH3:42])[O:38][C@H:39]([CH3:41])[CH2:40]2)=[C:20]([CH2:19][OH:18])[N:25]=[C:24]2[C:31]([CH3:33])=[N:30][O:29][C:23]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86658111HCID 86658111, compound2×

Product 1

HCID 67433810HCID 67433810, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

1-(6-((tert-Butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-(propan-2-ylideneaminooxy)pyridin-2-yl)ethanone (Intermediate 336, 821 mg, 1.35 mmol) was dissolved in 13 ml of EtOH. Aqueous 1M HCl, (4.33 ml, 4.33 mmol) was added to give an immediate precipitate, which dissolved to give a hazy yellow solution. The mixture was heated at 75° C. After 1 hour, 15 minutes, the reaction was cooled and diluted with EtOAc. Added saturated NaHCO3 to quench was followed by extraction 2× with EtOAc. The combined organic phase was dried over MgSO4 and concentrated. The crude was purified on SiO2 using 15-40% EtOAc/hexanes. Recovered 389 mg (88%) of the title compound as white solid.

Workup

  1. customto give an immediate precipitate, which
  2. dissolutiondissolved
  3. customto give a hazy yellow solution
  4. temperature15 minutes, the reaction was cooled
  5. customAdded saturated NaHCO3 to quench
  6. extractionwas followed by extraction 2× with EtOAc
  7. dry with materialThe combined organic phase was dried over MgSO4
  8. concentrationconcentrated
  9. customThe crude was purified on SiO2 using 15-40% EtOAc/hexanes
  10. customRecovered 389 mg (88%) of the title compound as white solid

Sources & evidence

ORD record
ord-5fde54ac39874bb7bd17a62b5666c5be
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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