Methanesulfonyl chloride → HCID 76689234, compound

HRID 390089Notes

Reaction equation

HRID 390089 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH:12]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH:13]1[CH2:20]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:32][S:33](Cl)(=O)=O.C[S-].[Na+]>ClCCl.CN(C=O)C.CCOC(C)=O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH:12]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH:13]1[CH2:20][S:33][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 76689230HCID 76689230, compound

Product 1

HCID 76689234HCID 76689234, compoundYield 86.4%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl((4RS,5RS)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methylcarbamate (0.884 g, 2.86 mmol) in dry dichloromethane (30 mL) was added diisopropylethylamine (1.417 ml, 8.57 mmol) and then methanesulfonyl chloride (0.288 ml, 3.71 mmol) and the solution was stirred at RT. After 30 mins the reaction mixture was washed with water, dil HCl and then sat aq NaHCO3. Normal processing afforded a syrup, which was dissolved in DMF (15 mL) and then sodium thiomethoxide (0.601 g, 8.57 mmol) was added with stirring. After 1 h, toluene was added and the mixture was washed with water (×2) and processed normally. Chromatography (EtOAc/Hex 1:2) gave benzyl((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (0.839 g, 2.472 mmol, 86% yield) as a syrup. 13C NMR (CDCl3) δ 156.9, 136.8, 128.9, 128.6, 128.5, 99.2, 72.3, 67.3, 62.4, 40.4, 39.9, 38.4, 29.0, 20.3, 17.3.

Workup

  1. washAfter 30 mins the reaction mixture was washed with water, dil HCl
  2. customNormal processing afforded a syrup, which
  3. washthe mixture was washed with water (×2)

Sources & evidence

ORD record
ord-3240961340144a03a51818096f153eaa
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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