Lithium Hydroxide → HCID 58468018, compound

HRID 1879385Notes

Reaction equation

HRID 1879385 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[C@@H:35]1[CH2:45][CH2:44][C@@H:43]([OH:46])[C:38]2=[N:39][CH:40]=[CH:41][CH:42]=[C:37]2[C@H:36]1[NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51].[OH-].[Li+]>O.O1CCCC1>[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[C@@H:35]1[CH2:45][CH2:44][C@H:43]([OH:46])[C:38]2=[N:39][CH:40]=[CH:41][CH:42]=[C:37]2[C@H:36]1[NH:47][C:48](=[O:54])[O:49][C:50]([CH3:52])([CH3:51])[CH3:53]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 61084-Nitrobenzoic AcidHCID 5363146Diisopropyl azodicarboxylateHCID 584679881289024-48-1

Product 1

HCID 58468018HCID 58468018, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

DIAD (0.356 mL, 1.833 mmol) was added to a tetrahydrofuran (5 mL) solution of 4-nitrobenzoic acid (0.306 g, 1.833 mmol), tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.3578 g, 0.916 mmol) at 0° C. The reaction was stirred overnight while it was gradually warmed up to room temperature. Lithium hydroxide (0.110 g, 4.58 mmol) in 10 mL water was added to the reaction mixture. The reaction was stirred at room temperature for 5 h. Volatile components were removed via vacuum and the crude residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed two more times by water before dried (sodium sulfate), filtered and concentrated. The crude was purified by flash chromatography eluting with ethyl acetate in hexane from 0 to 100%. The product was contaminated with some triphenyl phosphine oxide but was carried on to the next step without further purification: MS(ESI)[M+H+]=391.15.

Workup

  1. stirringThe reaction was stirred at room temperature for 5 h
  2. customVolatile components were removed via vacuum
  3. customthe crude residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed two more times by water
  5. dry with materialbefore dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by flash chromatography
  9. washeluting with ethyl acetate in hexane from 0 to 100%
  10. customwas carried on to the next step without further purification

Sources & evidence

ORD record
ord-05dd3b93dc12466898bbde8836b452ef
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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