Sodium Thiosulfate → HCID 22246956, compound

HRID 890730Notes

Reaction equation

HRID 890730 reaction equation
[OH:1][CH:2]([C:8]1[CH:28]=[CH:27][C:11]([CH2:12][N:13]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[C:2]([C:8]1[CH:28]=[CH:27][C:11]([CH2:12][N:13]([S:23]([CH3:26])(=[O:24])=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:10][CH:9]=1)(=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 10223499HCID 10223499, compound

Product 1

HCID 22246956HCID 22246956, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-{[4-(1-hydroxy-hexyl)-benzyl]-methanesulfonyl-amino}-heptanoic acid (88 mg, 0.21 mmol) and Dess-Martin reagent (145 mg, 0.34 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 72 h. Sodium thiosulfate solution was added and the reaction mixture was stirred until all solids were dissolved. The aqueous layer was extracted with CH2Cl2 (2×), and the organic solution was dried over MgSO4, filtered, and concentrated in vacuo. Purification by radial chromatography (CH2 Cl2to 5% MeOH/CH2Cl2) provided the title compound (93.6 mg). 1H NMR (400 MHz, CDCl3) δ 7.92 (d, 2H), 7.43 (d, 2H), 4.40 (s, 2H), 3.15 (t, 2H), 2.95 (t, 2H), 2.85 (s, 3H), 2.28 (t, 2H), 1.71 (m, 2H), 1.50 (m, 4H), 1.15–1.40 (m, 8H), 0.85–0.95 (m, 3H).

Workup

  1. dissolutionwere dissolved
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  3. dry with materialthe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by radial chromatography (CH2 Cl2to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-971153fe6fce49e4a7acdeb987e54749
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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