Methanesulfonyl chloride → HCID 88538049, compound

HRID 1476928Notes

Reaction equation

HRID 1476928 reaction equation
[OH:1][CH2:2][CH:3]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][OH:5].C(N(CC)C(C)C)(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:1][CH2:2][CH:3]([O:6][CH2:7][CH2:8][NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[CH2:4][O:5][S:27]([CH3:26])(=[O:29])=[O:28])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 77174860HCID 77174860, compound

Product 1

HCID 88538049HCID 88538049, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-3 °C

Procedure

A 20-L 4-neck round-bottom flask was flushed with N2, then charged a solution of tert-butyl 2-(1,3-dihydroxypropan-2-yloxy)ethylcarbamate (418 g, 1.8 mol, 1.0 eq) in dichloromethane (9000 mL, 21.5 v) and N,N-diisopropylethylamine (574 g, 4.4 mol, 2.5 eq). This is followed by dropwise addition of methanesulfonyl chloride (509 g, 4.4 mol, 2.5 eq) with stirring at −6-0° C. over 1 hour. The resulting mixture was stirred for 4 h at −6˜4° C., then washed with water (3×4000 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/EtOAc (1:1) to give 740 g (101.0%) of 2-(2-(tert-butoxycarbonylamino)ethoxy)propane-1,3-diyl dimethanesulfonate as a yellow oil.

Workup

  1. customA 20-L 4-neck round-bottom flask was flushed with N2
  2. stirringThe resulting mixture was stirred for 4 h at −6˜4° C.
  3. washwashed with water (3×4000 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. washeluted with petroleum ether/EtOAc (1:1)

Sources & evidence

ORD record
ord-676bdc54912c4495bf141d90d80bb79f
Source dataset
uspto-grants-2016_08
Patent number
US09402914B2

Reaction notes

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