Triacetoxyperiodinane → 3-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

HRID 2075813Notes

Reaction equation

HRID 2075813 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH:8]([NH:23][C:24](=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:9]([OH:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:44])[CH2:7][CH:8]([NH:23][C:24](=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:9](=[O:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 866130763-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Product 1

HCID 866130773-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Composition 15 (56 mg, 0.088 mmol) and Dess-Martin periodinane (48 mg, 0.114 mmol, 1.3 equiv) in DCM (2 mL) were added to a dry round bottom flask equipped with a magnetic stir bar. The cloudy white suspension was allowed to react for 20 minutes. Saturated NaHCO3 (20 ml) was added and the reaction was extracted with EtOAc (20 mL). The organic layer was dried over NaHCO3, concentrated in vacuo, and purified via column chromatography (silica gel, 1:1, hexanes/EtOAc) to give 16 (23 mg, 0.036 mmol, 64% yield) as a sticky white solid. ESMS: 635.4 (M+H+), 657.2 (M+Na+).

Workup

  1. customequipped with a magnetic stir bar
  2. customto react for 20 minutes
  3. extractionthe reaction was extracted with EtOAc (20 mL)
  4. dry with materialThe organic layer was dried over NaHCO3
  5. concentrationconcentrated in vacuo
  6. custompurified via column chromatography (silica gel, 1:1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-eab68077bacf4a509235d588d57d259b
Source dataset
uspto-grants-2011_04
Patent number
US07923433B2

Reaction notes

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