Triethylamine → HCID 86621625, compound

HRID 2246964Notes

Reaction equation

HRID 2246964 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][CH2:43][OH:44])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.S(=O)(=O)(O)[O-].[K+]>CS(C)=O.ClCCl.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][CH:43]=[O:44])[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 68440071HCID 68440071, compound

Product 1

HCID 86621625HCID 86621625, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4.29 g of 2-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethanol (from example 25e) in 6.0 ml of dimethylsulfoxide and 30 ml of dichloromethane at 0° C. are added 4.80 ml of triethylamine and 3.60 g of pyridine sulfur trioxide complex. The reaction mixture is allowed to stir for an additional 3 hours at this temperature and then allowed to warm to room temperature, diluted with water and acidified by the addition of 1N potassium bisulfate solution and subsequently extracted with diethyl ether. The organic phases are dried, concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a colourless oil. Rf=0.21 (EtOAc-heptane 1:1); Rt=4.82.

Workup

  1. extractionsubsequently extracted with diethyl ether
  2. customThe organic phases are dried
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-7f0c66ccb3854df39c8f42d820a1e63f
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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