Triethylamine → Acetate

HRID 1881346Notes

Reaction equation

HRID 1881346 reaction equation
CS(Cl)(=O)=[O:3].[C:6]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C>ClCCl>[C:17]([O-:18])(=[O:3])[CH3:14].[C:6]([NH:13][CH:14]([CH2:15][OH:16])[CH2:17][OH:18])([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10631565N-Boc-serinol

Product 2

HCID 175AcetateHCID 10631565N-Boc-serinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Methanesulfonyl chloride (130 mmol) was added at 5° C. to a stirred solution of boc-serinol (40 mol) and triethylamine (25 ml) in dichloromethane (100 ml). The mixture was stirred at 5° C. for 5 h and at 20° C. for 20 h. Dichloromethane (200 ml) was added and the mixture was washed with an aqueous solution of sodium hydrogen carbonate (50 mM), dried (Na2SO4) and concentrated to dryness under vacuum. Chromatography of the residue on silicagel (1.2 L) eluting with hexane/ethyl:acetate (50:50) gave bis-(methanesulfonic acid ester) of boc-serinol.

Workup

  1. washthe mixture was washed with an aqueous solution of sodium hydrogen carbonate (50 mM)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to dryness under vacuum
  4. washChromatography of the residue on silicagel (1.2 L) eluting with hexane/ethyl

Sources & evidence

ORD record
ord-b1999b5c4a054b7ab5a60dbf65f4ed67
Source dataset
uspto-grants-2012_11
Patent number
US08318795B2

Reaction notes

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