Triacetoxyperiodinane → HCID 178520412, compound

HRID 852786Notes

Reaction equation

HRID 852786 reaction equation
[C:1]12([NH:11][C:12]3[S:13][CH:14]([CH2:18][CH2:19][OH:20])[C:15](=[O:17])[N:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]12([NH:11][C:12]3[S:13][CH:14]([CH2:18][CH:19]=[O:20])[C:15](=[O:17])[N:16]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178517905HCID 178517905, compound

Product 1

HCID 178520412HCID 178520412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-(1-adamantylamino)-5-(2-hydroxyethyl)thiazol-4(5H)-one (0.25 g, 0.85 mmol) in CH2Cl2 (10 mL) was added to Dess-Martin periodinane (0.56 g, 1.28 mmol, Aldrich) in CH2Cl2 (10 mL). After stirring at ambient temperature for 1 h, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous sodium thiosulfate and aqueous sodium bicarbonate. The organic portion was separated, washed with brine, and conc. in vacuo to give the title compound as a light yellowish solid. MS m/z: 293.6 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium thiosulfate and aqueous sodium bicarbonate
  3. customThe organic portion was separated
  4. washwashed with brine

Sources & evidence

ORD record
ord-7047958e005e4b96a730e95bca33b9bd
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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