Diazomethane → HCID 68441200, compound

HRID 2246952Notes

Reaction equation

HRID 2246952 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][C:43]([OH:45])=[O:44])[CH2:10]2)=[CH:5][CH:4]=1.[N+](=[CH2:48])=[N-].S([O-])([O-])(=O)=O.[Mg+2]>CO.CCOCC>[CH3:48][O:44][C:43](=[O:45])[CH2:42][C@H:11]1[CH2:10][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]3[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=3[CH:31]=2)[CH2:13][N:12]1[S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)(=[O:33])=[O:34]

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 68439434HCID 68439434, compound

Product 1

HCID 68441200HCID 68441200, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.03 g of [(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]-acetic acid (from example 25f) in 50 ml of methanol at 0° C. is added a 0.1M solution of diazomethane in ether until the conversion to the methyl ester is complete. The reaction mixture is treated with magnesium sulfate to destroy the excess of 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 as a yellow oil. Rf=0.24 (EtOAc-heptane 1:1); Rt=5.24.

Workup

  1. customto destroy the excess of 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-e16f618c378f42e6875ad07a6b58a1c4
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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