HCID 13653855, compound → HCID 23321717, compound

HRID 280090Notes

Reaction equation

HRID 280090 reaction equation
[C:1]([CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])([OH:3])=[O:2].I([O-])(=O)(=O)=[O:15].[Na+]>CO.O.C(#N)C>[C:1]([CH2:4][S:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:15])([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 13653855HCID 13653855, compoundHCID 23667635Sodium periodate

Product 1

HCID 23321717HCID 23321717, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

A chilled solution of 4.12 g of the 6-(carboxymethylthio)hexanoic acid of Example 1(a) in 130 ml MeOH was mixed with a chilled solution of 4.28 g sodium meta-periodate in 320 ml water. The mixture was maintained at about 5° C. for two days, after which it was diluted with two volumes of cold acetonitrile. Solid sodium iodate was removed by filtration and the filtrate was concentrated to an oily residue under reduced pressure. The oil was characterized by NMR and was not further purified. NMR (in Unisol-D): 10.2-10.5 (S, 2, COOH), 3.6-3.8 (S, 2, S(O)--CH2 --COOH), 2.7-3.1 (M, 2, --CH2 --S(O), 2.1-2.5 (M, 2, --CH2 --COOH), 1.4-1.9 (M, 6, --CH2 --) (also a small peak at=4.0 indicating some sulfone present).

Workup

  1. customSolid sodium iodate was removed by filtration
  2. concentrationthe filtrate was concentrated to an oily residue under reduced pressure

Sources & evidence

ORD record
ord-9fb16c8800df44eeba8d4831c6b9c6e7
Source dataset
uspto-grants-1986_05
Patent number
US04588718

Reaction notes

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