Nitric Acid → HCID 18660185, compound

HRID 1292209Notes

Reaction equation

HRID 1292209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:24][C:25]([OH:27])=[O:26])[C:5]2[O:10][C@@H:9]([CH2:11][O:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:8][O:7][C:6]=2[CH:23]=1.[N+:28]([O-])([OH:30])=[O:29]>ClC(Cl)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([N+:28]([O-:30])=[O:29])=[C:4]([CH2:24][C:25]([OH:27])=[O:26])[C:5]2[O:10][C@@H:9]([CH2:11][O:12][S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH2:8][O:7][C:6]=2[CH:23]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 18660184HCID 18660184, compound

Product 1

HCID 18660185HCID 18660185, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

To 3.0 g (7.3 mmole) of (R)-(7-chloro-3-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo(1,4)dioxin-5-yl)-acetic acid in 50 of dichloroethane in an ice/water bath was added a solution of 3.6 ml (85 mmole) of nitric acid (sp. gr. 1.49) in 50 ml of dichloroethane. The mixture was allowed to come to room temperature and stir overnight. Ice was added to quench the reaction and the mixture was diluted to 300 ml with methylene chloride, washed with water and with saturated brine and dried over sodium sulfate. Concentration in vacuum gave 2.8 g of the title compound as an off-white solid. 1H (DMSO-d6) broad singlet, 12.75 δ(1 H); doublet, 7.80 δ(2 H); doublet, 7.45 δ(2 H);.singlet, 7.15 δ(1 H); multiplet, 4.60 δ(1 H); multiplet, 4.37 δ(2 H); multiplet, 4.15 δ(2 H); singlet, 3.45 δ(2H); singlet, 2.40 δ(3 H).

Workup

  1. customto come to room temperature
  2. additionIce was added
  3. customto quench
  4. customthe reaction
  5. washwashed with water and with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationConcentration in vacuum

Sources & evidence

ORD record
ord-d50be957d36145719e133618465fe185
Source dataset
uspto-grants-1998_05
Patent number
US05756532

Reaction notes

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