4-Mercaptobenzoic acid → HCID 13325393, compound

HRID 1262956Notes

Reaction equation

HRID 1262956 reaction equation
[Na].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)([OH:4])=[O:3].[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][O:18][C@@H:17]1Cl)(=[O:14])[CH3:13]>CN(C)C=O>[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][O:18][C@H:17]1[S:11][C:8]1[CH:9]=[CH:10][C:5]([C:2]([OH:4])=[O:3])=[CH:6][CH:7]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 957384-Mercaptobenzoic acidHCID 5360545SodiumHCID 12942066HCID 12942066, compound

Product 1

HCID 13325393HCID 13325393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 19.8 g. of sodium salt of paracarboxythiophenol in dimethylformamide solution was added 29.5 g of tri-O-acetyl-α-D-xylosylchloride (4). After the resulting reaction mixture was allowed to stand overnight, the dimethylformamide was distilled away and the resulting residue was extracted with ethyl acetate. The obtained organic layer was washed with water, followed by drying over anhydrous magnesium sulfate. When the solvent was distilled away, white powdery paracarboxyphenyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (10) was obtained. To 144 ml. of anhydrous methanol were added 12.0 g. of the obtained paracarboxyphenyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (10) and 720 mg. of lithium hydroxide, and the mixture was allowed to stand overnight at room temperature. Then, the reaction mixture was diluted with water and was passed through an acidic resin in the usual way. The solution which has thus been passed was adjusted to pH 7.0 by adding sodium hydroxide. The so neutralized solution was concentrated to yield 8 g. of the desired para(sodiumoxycarbonyl)phenyl 1-thio-β-D-xylopyranoside in the state of white powder.

Workup

  1. customAfter the resulting reaction mixture
  2. distillationthe dimethylformamide was distilled away
  3. extractionthe resulting residue was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationWhen the solvent was distilled away

Sources & evidence

ORD record
ord-ff1629ad03c74a68ac329f7dc3edfc61
Source dataset
uspto-grants-1984_06
Patent number
US04454123

Reaction notes

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