Tetrahydrofuran → HCID 67390682, compound

HRID 910474Notes

Reaction equation

HRID 910474 reaction equation
[CH2:1]([O:3][C@H:4]([CH3:50])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([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)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@H:16](CC=O)[CH2:15]2)=[CH:10][CH:9]=1)[CH3:2].C[Mg]Br.[CH2:54]1[CH2:58][O:57]CC1>S([O-])(O)(=O)=O.[K+]>[CH2:1]([O:3][C@H:4]([CH3:50])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([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)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:38])=[O:39])[C@H:16]([CH2:25][C@H:26]([NH:27][C:58](=[O:57])[CH3:54])[CH3:36])[CH2:15]2)=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86649418HCID 86649418, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67390682HCID 67390682, compound

Reagents, catalysts & solvents 1

HCID 516920Potassium bisulfateSolvent

Procedure

To a stirred solution of 1.0 mmol [(2S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl) -phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde in 10 ml of THF are added 2.0 mmol of methyl magnesium bromide (3M in THF) at 0° C. The reaction mixture is allowed to warm to RT and stirred for 1 h, diluted with an aqueous solution of 1N potassium hydrogen sulfate and extracted with TBME. The organic phases are combined and dried over Na2SO4. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound, which is identified based on its Rf value.

Workup

  1. extractionextracted with TBME
  2. dry with materialdried over Na2SO4
  3. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-3caabe171bb5434cb024e21b51afba1b
Source dataset
uspto-grants-2011_09
Patent number
US08022069B2

Reaction notes

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