Water → HCID 23449785, compound

HRID 348416Notes

Reaction equation

HRID 348416 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].O>N1C=CC=CC=1>[CH3:1][S:2]([O:6][CH2:7][CH2:8][N:9]([C:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:16])[CH3:17])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 23449785HCID 23449785, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (2.98 ml, 38.6 mmol) was added to an ice-cold solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (Synth. Commun. 1993; 23(17); 2443) (4.5 g, 25.7 mmol) in pyridine (40 ml), and the reaction stirred for 2 hours. The solution was poured into water (150 ml), and extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with 10% aqueous citric acid solution, dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (34:66 to 40:60) to give the title compound, 1.0 g.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washThe combined organic extracts were washed with 10% aqueous citric acid solution
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (34:66 to 40:60)

Sources & evidence

ORD record
ord-779c975a8a6e45a798e7b1f314274824
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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