Tert-Butyl hypochlorite → HCID 56966444, compound

HRID 1770732Notes

Reaction equation

HRID 1770732 reaction equation
[CH3:1][C:2]1([CH2:8][S:9]([CH2:12][CH:13]([OH:18])[CH:14]([OH:17])[CH2:15][OH:16])(=[O:11])=[O:10])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.C(O[Cl:24])(C)(C)C>CO>[Cl:24][N:3]1[C:2]([CH3:1])([CH2:8][S:9]([CH2:12][CH:13]([OH:18])[CH:14]([OH:17])[CH2:15][OH:16])(=[O:11])=[O:10])[CH2:6][O:5][C:4]1=[O:7]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67515307HCID 67515307, compound

Product 1

HCID 56966444HCID 56966444, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methyl-4-((2,3,4-trihydroxybutylsulfonyl)methyl)oxazolidin-2-one (990 mg, 3.49 mmol) in methanol (5 ml) was cooled to 0° C. and tert-butylhypochlorite (400 ul, 3.35 mmol) was added drop-wise. The solution was stirred for 2 hours, concentrated in vacuo, and the residue purified by flash chromatography (5% to 20% methanol in dichloromethane) to afford the title compound as a mixture of diastereomers (364.5 mg, 1.147 mmol, 33%). 1H NMR (D2O, 400 MHz) δ 1.50 (s, 3H), 3.3-4.3 (m, 7H), 4.4-4.5 (m, 1H), 4.9-5.0 (m, 1H); LRMS (ESI/APCI) m/z 318 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (5% to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-65391adcf3324716b149c7e106a20fdb
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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