Methanesulfonyl chloride → HCID 86651336, compound

HRID 390088Notes

Reaction equation

HRID 390088 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][CH:5]([CH:7]([CH2:20]O)[CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][O: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>[CH3:1][C:2]1([CH3:22])[O:6][CH:5]([CH:7]([CH2:20][S:33][CH3:32])[CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][O:3]1

Participants

9

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 76741568benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate

Product 1

HCID 86651336HCID 86651336, compoundYield 83.1%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate (0.843 g, 2.73 mmol) in dry dichloromethane (30 mL) was added diisopropylethylamine (1.351 ml, 8.18 mmol) and then methanesulfonyl chloride (0.274 ml, 3.54 mmol) and the resulting solution was stirred at RT. After 15 mins it was washed with water, dil HCl, and sat aq NaHCO3 and then processed normally. A solution of the crude product in DMF (15 mL) was treated with sodium thiomethoxide (0.573 g, 8.18 mmol) and the mixture was stirred at RT for 1 h. Then toluene was added and the mixture was washed with water (×2) and processed normally. Chromatography (EtOAc/Hex 1:2) gave benzyl (SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propylcarbamate (0.77 g, 2.268 mmol, 83% yield) as a syrup. 13C NMR (CDCl3) δ156.9, 136.9, 128.9, 128.5, 128.5, 109.3, 76.8, 67.7, 67.1, 41.9, 33.7, 26.9, 25.6, 16.6.

Workup

  1. washAfter 15 mins it was washed with water, dil HCl
  2. washthe mixture was washed with water (×2)

Sources & evidence

ORD record
ord-446e37d309e74ef6ae34843520cd70b0
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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