HCID 86621619, compound → HCID 68442068, compound

HRID 2246940Notes

Reaction equation

HRID 2246940 reaction equation
CON(C)[C:4](=[O:47])[CH2:5][C@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:8][N:7]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38].[CH3:49][Mg]Br>O1CCCC1.S([O-])(O)(=O)=O.[K+]>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C@@H:10]2[C@@H:9]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:8][N:7]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:38])=[O:39])[C@@H:6]([CH2:5][C:4](=[O:47])[CH3:49])[CH2:11]2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 86621619HCID 86621619, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68442068HCID 68442068, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516920Potassium bisulfateSolvent

Procedure

To a stirred solution of 0.79 g of N-methoxy-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]-N-methyl-acetamide in 10 ml of tetrahydrofuran are added 1.3 ml of a 3M solution of methyl magnesium bromide in tetrahydrofuran at 0° C. The reaction mixture is stirred for 1 hour, diluted with an aqueous solution of 1N potassium hydrogen sulfate, extracted with tert-butyl methyl ether. The organic phases are combined and dried over sodium sulfate. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow oil. Rf=0.20 (EtOAc-heptane 1:1); Rt=5.14.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. dry with materialdried over sodium sulfate
  3. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-785278634daa4d91a57ebf049c8a098c
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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