Methanesulfonyl chloride → Methyl 3-([2-(2,6-bis-methanesulfonyloxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-propanoate

HRID 2173755Notes

Reaction equation

HRID 2173755 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][N:12]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:5]([CH2:29][OH:30])[N:4]=1.C(N(C(C)C)CC)(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:40][S:41]([O:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][N:12]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:5]([CH2:29][O:30][S:41]([CH3:40])(=[O:43])=[O:42])[N:4]=1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66713832Methyl 3-([2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-propanoate

Product 1

HCID 87120706Methyl 3-([2-(2,6-bis-methanesulfonyloxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 80 mg of methyl 3-([2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-propanoate in 8 ml of DCM, precooled to −25° C., was added 183 μl of diisopropylethylamine and 57 μl of methanesulfonyl chloride. The mixture was stirred for 1 hour at −15° C. and then washed with 5 ml of water. The aqueous phase was extracted with 5 ml of DCM. The organic phases were combined, dried over MgSO4 and concentrated under reduced pressure. 110 mg of methyl 3-([2-(2,6-bis-methanesulfonyloxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-propanoate were obtained. LC/MS (B): tr=2.67 min; [M+H]+: m/z 587

Workup

  1. customprecooled to −25° C.
  2. washwashed with 5 ml of water
  3. extractionThe aqueous phase was extracted with 5 ml of DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a2af483ac7a4c1594bd646dfc2cc6ae
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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