Triethylamine → HCID 131726739, compound

HRID 2252388Notes

Reaction equation

HRID 2252388 reaction equation
[NH2:1][C@@H:2]1[CH2:15][CH2:14][C@:13]2([OH:16])[C@:4]34[CH2:19][CH2:18][N:17]([CH2:20][CH:21]5[CH2:23][CH2:22]5)[C@@H:12]2[CH2:11][C:10]2[CH:9]=[CH:8][C:7]([O:24][CH2:25][O:26][CH3:27])=[C:6]([O:28][C@@H:3]13)[C:5]4=2.C(N(CC)CC)C.[C:36]1([S:46](Cl)(=[O:48])=[O:47])[C:37]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:39]=[CH:40][CH:41]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH:21]1([CH2:20][N:17]2[CH2:18][CH2:19][C@:4]34[C:5]5[C:6]6[O:28][C@H:3]3[C@H:2]([N:1]3[S:46](=[O:48])(=[O:47])[C:36]7[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=7[S:42]3(=[O:44])=[O:43])[CH2:15][CH2:14][C@@:13]4([OH:16])[C@H:12]2[CH2:11][C:10]=5[CH:9]=[CH:8][C:7]=6[O:24][CH2:25][O:26][CH3:27])[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 246432Benzene-1,2-disulfonyl dichlorideHCID 516892Sodium BicarbonateHCID 69299212HCID 69299212, compound

Product 1

HCID 131726739HCID 131726739, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 mL of dichloromethane, 117 mg (0.30 mmol) of 6β-amino-17-cyclopropylmethyl-4,5α-epoxy-3-methoxymethoxy-morphinan-14-ol was dissolved, and 0.04 mL (0.29 mmol) of triethylamine and 79 mg (0.31 mmol) of benzene-1,2-disulfonyl dichloride were added, followed by heating the mixture to reflux for 1 hour. After allowing the reaction solution to cool to room temperature, aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain 192 mg of 2-(17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-3-methoxymethoxy-morphinan-6β-yl)-benzo[1,3,2]dithiazol-1,1,3,3-tetroxide as a crude product.

Workup

  1. temperatureby heating the mixture
  2. temperatureto reflux for 1 hour
  3. extractionthe resulting mixture was extracted with chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a287336c7d05493984d7cefcc44be465
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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