Sodium Thiosulfate Pentahydrate → HCID 86660405, compound

HRID 1186137Notes

Reaction equation

HRID 1186137 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C@:11]([NH:16][S@@:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])([CH3:15])[CH2:12][CH2:13][OH:14].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OC(=O)C)C.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C@:11]([NH:16][S@@:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])([CH3:15])[CH2:12][CH:13]=[O:14]

Participants

8

Reactant 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67466787HCID 67466787, compound

Product 1

HCID 86660405HCID 86660405, compoundYield 1,445.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-3-hydroxy-1-methyl-propyl]-amide (intermediate A4C) (1.1 g, 3.3 mmol) in anhydrous CH2Cl2 (35 ml) at 23° C. was added Dess-Martin Periodinan (1.825 g, 4.3 mmol) and the mixture was stirred at 23° C. for 3 h. Reaction mixture was poured into 20 mL of a 1M aqueous NaHCO3 solution containing 2 g of sodium thiosulfate, pentahydrate and the mixture was stirred at 23° C. for 15 min. The two phases were separated, the collected organic phase was dried over Na2SO4 and removal of the solvent in vacuum left a residue. Purification of the residue was performed by chromatography on silica using a mixture of Heptane and a solution of 3% Triethylamine in Ethylacetate which yielded the (R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-1-methyl-3-oxo-propyl]-amide (970 mg, 47.7 mmol, 88% yield) as a off-white solid. MS (ISP): m/z=331.1 [(M+H)+].

Workup

  1. customReaction mixture
  2. stirringthe mixture was stirred at 23° C. for 15 min
  3. customThe two phases were separated
  4. dry with materialthe collected organic phase was dried over Na2SO4 and removal of the solvent in vacuum
  5. waitleft a residue
  6. customPurification of the residue
  7. additiona mixture of Heptane

Sources & evidence

ORD record
ord-91dd9fe6135f44eb8c25628b7c6f2b21
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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