Triethylamine → (R)-4-Ethylamino-3,4-dihydro-2-(2-hydroxyethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

HRID 1081284Notes

Reaction equation

HRID 1081284 reaction equation
Cl.[CH2:2]([NH:4][C@@H:5]1[C:10]2[CH:11]=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[S:13][C:9]=2[S:8](=[O:19])(=[O:18])[N:7]([CH2:20][CH2:21][O:22]C)[CH2:6]1)[CH3:3].C(N(CC)CC)C.BrB(C)C>ClCCCl>[CH2:2]([NH:4][C@@H:5]1[C:10]2[CH:11]=[C:12]([S:14]([NH2:17])(=[O:15])=[O:16])[S:13][C:9]=2[S:8](=[O:18])(=[O:19])[N:7]([CH2:20][CH2:21][OH:22])[CH2:6]1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123224DimethylboronbromideHCID 228466652H-Thieno(3,2-E)-1,2-thiazine-6-sulfonamide, 4-(ethylamino)-3,4-dihydro-2-(2-methoxyethyl)-, 1,1-dioxide, monohydrochloride, (R)-

Product 1

HCID 54385002(R)-4-Ethylamino-3,4-dihydro-2-(2-hydroxyethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxideYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of (R)-(+)-4-Ethylamino-3,4-dihydro-2-(2-methoxyethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide hydrochloride (6.03 g, 15.0 mmol) in 1,2-dichloroethane (50 mL) was added triethylamine (210 mL, 1.5 mmol) followed by bromodimethylborane (5.79 mL, 59.0 mmol) at 0° C. After 4 h at room temperature, the reaction was quenched by adding a saturated aqueous solution of sodium bicarbonate; this mixture was extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4) and evaporated to give the desired alcohol product as a syrup (4.8 g, 91%).

Workup

  1. customthe reaction was quenched
  2. additionby adding a saturated aqueous solution of sodium bicarbonate
  3. extractionthis mixture was extracted with ethyl acetate (4×50 mL)
  4. washThe combined extracts were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-743a2e4f62e24d8c9394ae198cd372b0
Source dataset
uspto-grants-1996_12
Patent number
US05585377

Reaction notes

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