Diazomethane → HCID 68442607, compound

HRID 2246961Notes

Reaction equation

HRID 2246961 reaction equation
[N+](=[CH2:3])=[N-].C(OCC)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:22][C@H:21]([CH2:23][C@H:24]([C:27]3[NH:31][N:30]=[N:29][N:28]=3)[CH2:25][CH3:26])[NH:20][CH2:19][C@@H:18]2[O:32][CH:33]([C:44]2[CH:45]=[CH:46][C:47]3[O:52][CH2:51][CH2:50][N:49]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:48]=3[CH:58]=2)[S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[CH:13][CH:12]=1.S([O-])([O-])(=O)=O.[Mg+2].[N+](=C)=[N-]>CO>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:22][C@H:21]([CH2:23][C@H:24]([C:27]3[N:28]([CH3:3])[N:29]=[N:30][N:31]=3)[CH2:25][CH3:26])[NH:20][CH2:19][C@@H:18]2[O:32][CH:33]([C:44]2[CH:45]=[CH:46][C:47]3[O:52][CH2:51][CH2:50][N:49]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:48]=3[CH:58]=2)[S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:35])=[O:36])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 9550DiazomethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21186548Diazomethane diethyletherHCID 178455881HCID 178455881, compound

Product 1

HCID 68442607HCID 68442607, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A freshly prepared solution of diazomethane/diethylether (from Diazald®) is added dropwise to a solution of 0.201 g of 6-[(3R,4R,6S)-4-(4-methoxy-phenyl)-6-[(R)-2-(1H-tetrazol-5-yl)-butyl]-1-(toluene-4-sulfonyl)-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine (from example 64a) in 8 ml of methanol at 0° C. After 2.5 hours, solid magnesium sulfate is added to decompose any excess diazomethane and then the reaction mixture is concentrated. The resulting residue is suspended in dichloromethane, filtered and re-concentrated. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound together with its N-methylated regioisomer.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. filtrationfiltered
  3. concentrationre-concentrated
  4. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-3e3a3e6b4a94466c97978a7cff3aacb7
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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