Triacetoxyperiodinane → HCID 117982171, compound

HRID 1776110Notes

Reaction equation

HRID 1776110 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH2:18][OH:19])[C@@H:12]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:11]([CH3:27])[O:10][C:9]1=[O:28])([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:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH:18]=[O:19])[C@@H:12]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:11]([CH3:27])[O:10][C:9]1=[O:28])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117982168HCID 117982168, compound

Product 1

HCID 117982171HCID 117982171, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl((3S,7R,8R,9S)-7-(2-hydroxyethyl)-9-methyl-2-oxo-8-phenoxyoxonan-3-yl)carbamate (250 mg, 0.613 mmol) in CH2Cl2 (6.1 mL) at 0° C. was added Dess-Martin periodinane (286 mg, 0.675 mmol). The resulting mixture was stirred at 0° C. for 2 h, quenched with sat. aqueous sodium thiosulfate (Na2S2O3; 3 mL) and sat. aqueous NaHCO3 (3 mL) solution, and then removed from the cold bath and stirred vigorously for 10 min. The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×6 mL) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated to provide the title compound as a fluffy white foam (255.4 mg, 98%): 1H NMR (400 MHz, CDCl3) δ 9.65 (t, J=1.7 Hz, 1H), 7.29 (dd, J=8.7, 7.4 Hz, 2H), 7.02-6.93 (m, 1H), 6.88 (d, J=7.9 Hz, 2H), 5.23-5.08 (m, 2H), 4.30-4.10 (m, 2H), 2.60 (dd, J=16.0, 5.4 Hz, 1H), 2.44 (d, J=6.4 Hz, 1H), 2.38-2.21 (m, 2H), 1.73 (ddd, J=19.5, 13.8, 9.2 Hz, 3H), 1.44 (s, 9H), 1.37-1.22 (m, 5H); 13C NMR (101 MHz, CDCl3) δ 200.78, 173.29, 158.65, 154.90, 129.80, 129.73, 121.59, 115.23, 80.63, 79.98, 74.23, 53.28, 46.09, 36.71, 33.64, 31.78, 28.33, 19.72, 18.18; ESIMS m/z 428.2 ([M+Na]+).

Workup

  1. customquenched with sat. aqueous sodium thiosulfate (Na2S2O3; 3 mL) and sat. aqueous NaHCO3 (3 mL) solution
  2. customremoved from the cold bath
  3. stirringstirred vigorously for 10 min
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CH2Cl2 (2×6 mL)
  6. dry with materialthe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-572c660f6a4444b8990daa7c6bdea877
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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