Sodium Thiosulfate → HCID 11164385, compound

HRID 2266899Notes

Reaction equation

HRID 2266899 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C@H:11]([CH:19]([OH:21])[CH3:20])[C@H:12]([CH3:18])[CH2:13][C:14]([F:17])([F:16])[F:15])(=[O:9])=[O:8])=[CH:4][CH:3]=1.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.CCOCC.C(=O)(O)[O-].[Na+].O.CCOC(C)=O.CCCCCC>[C:19]([C@@H:11]([NH:10][S:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:8])[C@H:12]([CH3:18])[CH2:13][C:14]([F:17])([F:16])[F:15])(=[O:21])[CH3:20]

Participants

9

Reactant 3

HCID 24477Sodium Thiosulfate2×HCID 159087TriacetoxyperiodinaneHCID 11187688HCID 11187688, compound

Product 1

HCID 11164385HCID 11164385, compoundYield 73.1%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5-chloro-N-[(1S,2R)-4,4,4-trifluoro-1-(1-hydroxyethyl)-2-methylbutyl]thiophene-2-sulfonamide (0.390 g, 1.06 mmol) in CH2Cl2 saturated with water (30 mL) was stirred under nitrogen at 0° C. Dess-Martin periodinane reagent (0.95 g, 2.23 mmol) was added in one portion. The resulting suspension was stirred at 25° C., monitoring the progress of reaction by TLC analysis (1:2 EtOAc/hexane). As the rate of conversion of the starting material slowed, additional 1 mL portions of CH2Cl2 saturated with water were added (three portions over 15 min). After 19 h at 25° C., the reaction was complete by TLC. The solution was diluted with Et2O (50 mL) and a solution of sodium thiosulfate, Na2S2O3 (11.83 mmol, 4.8 g, 11 eq) in 80% saturated aqueous sodium bicarbonate solution (40 mL) was added. The mixture was stirred rapidly for 10 min until both phases were clear. The layers were separated and the aqueous phase was extracted with ether (20 mL). The combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate (10 mL) and brine (15 mL), then dried over MgSO4, filtered and concentrated to obtain a crude oil (0.38 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:6 EtOAc-hexanes, to afford N-[(1S,2R)-1-acetyl-4,4,4-trifluoro-2-methylbutyl]-5-chlorothiophene-2-sulfonamide as a white solid (0.265 g, 73.10%). Mass Spectrum (−ESI): 362 (M−H)−.

Workup

  1. stirringThe mixture was stirred rapidly for 10 min until both phases
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ether (20 mL)
  4. washThe combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate (10 mL) and brine (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a crude oil (0.38 g)
  9. customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

Sources & evidence

ORD record
ord-ab4808ec859647f7894bb44962911371
Source dataset
uspto-grants-2010_12
Patent number
US07858658B2

Reaction notes

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