Hydrochloric Acid → HCID 117736397, compound

HRID 1482295Notes

Reaction equation

HRID 1482295 reaction equation
Cl.[Si]([O:9][CH:10]([CH2:14][S:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([OH:13])=[O:12])(C(C)(C)C)(C)C>O1CCCC1>[C:17]([S:16][S:15][CH2:14][CH:10]([OH:9])[C:11]([OH:13])=[O:12])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131736700HCID 131736700, compound

Product 1

HCID 117736397HCID 117736397, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 1 N aqueous hydrochloric acid solution (300 μl) was added to a solution of 2-(tert-butyldimethylsilyloxy)-3-(tert-butyldisulfanyl)propionic acid prepared by the method known in the literature (J. Am. Chem. Soc. 2008, 130, 4919) (Compound 24) (30.0 mg, 0.092 mol) in tetrahydrofuran (THF) (300 μl) at room temperature, and the mixture was stirred at 60° C. for 16 hours. The reaction solution was purified by Reverse-phase silica-gel chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford 3-(tert-butyldisulfanyl)-2-hydroxypropanoic acid (H-tBuSSlac-OH) (Compound SP666) (7.4 mg, 54%).

Workup

  1. customprepared by the method
  2. customThe reaction solution was purified by Reverse-phase silica-gel chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)

Sources & evidence

ORD record
ord-873b375a57384d839f6b9808fe4ed1f5
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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