Hydrochloric Acid → HCID 67091467, compound

HRID 598734Notes

Reaction equation

HRID 598734 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]([OH:21])[C:18]([OH:20])=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.Cl>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:17](=[O:21])[C:18]([OH:20])=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 159087TriacetoxyperiodinaneHCID 67091209HCID 67091209, compound

Product 1

HCID 67091467HCID 67091467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a scintillation vial containing (5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-hydroxy-acetic acid (0.35 g, 1.2 mmol) was added 15 mL DCM followed by the addition of Dess-Martin periodinane (0.61 g, 1.44 mmol). The reaction mixture was allowed to stir at room temperature for 20 minutes and poured into a separatory funnel containing 30 mL 0.5 M HCl. The layers separated and the aqueous layer extracted twice more with 50 mL DCM. The combined organic layers were washed with Brine, dried over MgSO4 and concentrated under vacuum to afford the desired product (purity >80% by NMR). No further purification was attempted. Expected mass=286. Observed mass=287.

Workup

  1. additionpoured into a separatory funnel
  2. customThe layers separated
  3. extractionthe aqueous layer extracted twice more with 50 mL DCM
  4. washThe combined organic layers were washed with Brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c0f9fe00f2340ac98e06904b4dfb03c
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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