Sulfuric acid magnesium salt (1:1) → HCID 67061773, compound

HRID 910808Notes

Reaction equation

HRID 910808 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:52])[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]([CH2:47][CH2:48][C:49]([OH:51])=[O:50])[CH2:15]2)=[CH:10][CH:9]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:54].S([O-])([O-])(=O)=O.[Mg+2]>CO>[CH3:54][O:50][C:49](=[O:51])[CH2:48][CH2:47][C@H:16]1[CH2:15][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][O:6][CH2:5][C@@H:4]([CH3:52])[CH2:3][O:2][CH3:1])=[CH:9][CH:10]=2)[C@@H:19]([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)[CH2:18][N:17]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:38])=[O:39]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 167693TrimethylsilyldiazomethaneHCID 67061837HCID 67061837, compound

Product 1

HCID 67061773HCID 67061773, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 mmol of 3-[(2S,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionic acid in 5 ml of MeOH at 0° C. are added 5.0 mmol of TMS-diazomethane (2M in hexane) until the conversion to the methyl ester is complete. The reaction mixture is treated with magnesium sulfate to destroy the excess of TMS-diazomethane. The solids are removed by filtration and the organic layer is concentrated under reduced pressure. 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. customto destroy the excess of TMS-diazomethane
  2. customThe solids are removed by filtration
  3. concentrationthe organic layer is concentrated under reduced pressure
  4. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-224f5767fe184ab3889ee3aa228ade31
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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