Sodium Thiosulfate → HCID 22246956, compound

HRID 480275Notes

Reaction equation

HRID 480275 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 CH2Cl2 (2 mL) was stirred at room temperature for 72 h. Sodium thiosulfate solution aqueous layer was extracted with CH2Cl2 (2×), and the organic solution was dried over MgSO4, filtered, and concentrated in vacuo. Purification by radical chromatography (CH2Cl2to 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. extractionSodium thiosulfate solution aqueous layer was extracted with CH2Cl2 (2×)
  2. dry with materialthe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by radical chromatography (CH2Cl2to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f03c77974fa5402d8421e168eef30d3f
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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