Triethylamine → Methanesulfonic Acid 2-[(2,3-dihydro-benzo[1,4]dioxin-5-yl)-(2-methanesulfonyloxy-ethyl)-amino]-ethyl ester

HRID 9735Notes

Reaction equation

HRID 9735 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]([CH2:15][CH2:16][OH:17])[CH2:12][CH2:13][OH:14])[C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26]>C(Cl)Cl>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]([CH2:15][CH2:16][O:17][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:12][CH2:13][O:14][S:25]([CH3:28])(=[O:27])=[O:26])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 161155602-[(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-(2-hydroxy-ethyl)-amino]-ethanol

Product 1

HCID 11383877Methanesulfonic Acid 2-[(2,3-dihydro-benzo[1,4]dioxin-5-yl)-(2-methanesulfonyloxy-ethyl)-amino]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of II (39.6 g, 0.165 mol) and triethyl amine (69 mL, 0.5 mol) in methylene chloride (250 mL), chilled to 5° C. in an ice-bath, is added a solution of mesyl chloride (38 mL, 0.5 mol) in methylene chloride (50 mL). The addition is carried out over 0.5 h at temperature not exceeding 18° C. The ice-bath is removed and resulting suspension is stirred at ambient temperature for 1 h. At that time, TLC and HPLC showed disappearance of starting material. The reaction mixture is washed with water (1×150 mL) and 5% aqueous NaHCO3 solution (1×150 mL), dried with MgSO4 and concentrated to afford III as red oil, crude yield 67.0 g (102%). 1H NMR (CDCl3) δ 6.85 (m, 1H), 6.63 (m, 2H), 4.28 (m, 8H), 3.55 (t, J=7.5 Hz, 4H), 2.97 (s, 6H).

Workup

  1. additionThe addition
  2. customexceeding 18° C
  3. customThe ice-bath is removed
  4. customresulting suspension
  5. washThe reaction mixture is washed with water (1×150 mL) and 5% aqueous NaHCO3 solution (1×150 mL)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7de5138076c54710a85ef56f3fb895ce
Source dataset
uspto-grants-2006_08
Patent number
US07091349B2

Reaction notes

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