Triacetoxyperiodinane → tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

HRID 924391Notes

Reaction equation

HRID 924391 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]([C:24]2[C:33]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:32][C:31]3[C:26](=[CH:27][C:28]([CH:45]([OH:47])[CH3:46])=[CH:29][CH:30]=3)[N:25]=2)=[O:23])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:45]([C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[C:33]([NH:34][C:35]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:44])[C:24]([C:22]([NH:21][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[N:11]3[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10]3)=[O:23])=[N:25]2)=[CH:30][CH:29]=1)(=[O:47])[CH3:46]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86726871Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxyethyl)quinolin-3-yl]carbamate

Product 1

HCID 86726872tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxyethyl)quinolin-3-yl]carbamate (0.100 g, 0.156 mmol) (from Example 15, step 7) in DCM (0.50 mL) was mixed with a solution of Dess-Martin periodinane (0.099 g, 0.23 mmol) in DCM (0.50 mL, 7.8 mmol). The reaction mixture was stirred at room temperature for 18 h. The crude mixture was diluted with DCM and washed with aq. NaOH. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (100 mg, 100%). LCMS calc. for C35H39N6O6 (M+H)+: m/z=639.2. Found: 639.2.

Workup

  1. washwashed with aq. NaOH
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd787360a6fc4b639b37c87bb9640404
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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