Triacetoxyperiodinane → HCID 11990759, compound

HRID 1972333Notes

Reaction equation

HRID 1972333 reaction equation
[C:1]([NH:5][C:6](=[O:53])[NH:7][C@@H:8]([C:49]([CH3:52])([CH3:51])[CH3:50])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[N:20]=[C:19]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)[CH:18]=2)[CH2:13][C@H:12]1[C:34]([NH:36][C@@H:37]([CH2:46][CH2:47][CH3:48])[C@H:38]([OH:45])[C:39]([NH:41][CH:42]1[CH2:44][CH2:43]1)=[O:40])=[O:35])=[O:10])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[C:1]([NH:5][C:6](=[O:53])[NH:7][C@@H:8]([C:49]([CH3:52])([CH3:51])[CH3:50])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[N:20]=[C:19]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)[CH:18]=2)[CH2:13][C@H:12]1[C:34]([NH:36][C@@H:37]([CH2:46][CH2:47][CH3:48])[C:38](=[O:45])[C:39]([NH:41][CH:42]1[CH2:44][CH2:43]1)=[O:40])=[O:35])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57872112HCID 57872112, compound

Product 1

HCID 11990759HCID 11990759, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-2-carboxamide (2.0 g, 2.72 mmol) in methylene chloride (10 mL) was added the Dess-Martin Periodinane reagent (2.29 g, 5.44 mmol), and the reaction mixture was stirred at room temperature for 1 hour. Completion of the reaction was monitored by TLC analysis. Upon completion the reaction mixture was diluted with water (100 mL) and the organic layer was separated. The aqueous layer was washed with methylene chloride (2×30 mL), and the combined organic layers were washed with saturated sodium bisulfite (20 mL) followed by sodium bicarbonate solution (20 mL), and dried over sodium sulfate. The solution was filtered, the filtrate concentrated under reduced pressure, and the resulting residue was stirred with hexane (10 mL). The solid was filtered and dried to provide 1.75 g (87.8%) of (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-2-carboxamide as white solid (HPLC purity: 97.3% by area; HPLC retention time: 22.58 minutes).

Workup

  1. customthe organic layer was separated
  2. washThe aqueous layer was washed with methylene chloride (2×30 mL)
  3. washthe combined organic layers were washed with saturated sodium bisulfite (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. stirringthe resulting residue was stirred with hexane (10 mL)
  8. filtrationThe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-a49059ec9e9a4eb6a5e53ccb19409df0
Source dataset
uspto-grants-2013_04
Patent number
US08431733B2

Reaction notes

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